5-bromo-2-chloro-4’-ethoxydiphenylmethane CAS#: 461432-23-5; 凯望编码 (ChemWhat Code): 767411
Identification
| 英文名 | 5-bromo-2-chloro-4’-ethoxydiphenylmethane |
| IUPAC Name | 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene |
| 分子结构 |  |
| CAS编号 | 461432-23-5 |
| MDL Number | MFCD11042292 |
| 别名 | 461432-23-5 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene 4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether 5-Bromo-2-chloro-4′-ethoxydiphenylmethane 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene Benzene, 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]- MFCD11042292 2-(4-ethoxybenzyl)-4-bromo-1-chlorobenzene C15H14BrClO 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene; 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 5-bromo-2-chloro-4 inverted exclamation mark -ethoxydiphenylmethane SCHEMBL38150 DTXSID60433931 ZUNCHZBITMUSRD-UHFFFAOYSA-N BCP08717 CS-B0023 AKOS015917373 SB17549 AC-26384 DS-12747 SY025637 AM20040524 4-bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methane EN300-6735475 A849902 4-bromo-1-chloro-2-(4-ethoxyphenyl)methyl-benzene 4-BROMO-1-CHLORO-2-[(4-ETHOXYPHENYL)METHYL]-BENZENE |
| 分子式 | C15H14BrClO |
| 分子量 | 325.63 |
| InChI | InChI=1S/C15H14BrClO/c1-2-18-14-6-3-11(4-7-14)9-12-10-13(16)5-8-15(12)17/h3-8,10H,2,9H2,1H3 |
| InChI Key | ZUNCHZBITMUSRD-UHFFFAOYSA-N |
| Isomeric SMILES | CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)Br)Cl |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| CN117551153, | A method for the synthesis of dapagliflozin intermediates by continuous reaction | 2024 |
| CN115785045 | Photocatalytic Endagliflozin precursor and synthesis method thereof | 2023 |
| CN116120299 | Preparation method of 1-C-substituted phenyl glucopyranose carbon glycoside | 2023 |
| CN116789716 | Preparation method of dapagliflozin and etogliflozin intermediates | 2023 |
Physical Data
| Appearance | White to off -white solid powder |
| Melting Point, °C | Solvent (Melting Point) |
| 40 – 41 | ethanol |
| 40 – 42 | |
| 42 – 45 | |
| 38 – 40 | |
| 39 – 41 | |
| 40 – 41 | |
| 37 | ethanol |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | |
| Chemical shifts | 1H | chloroform-d1 | |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 400 |
Route of Synthesis (ROS)
| Conditions | Yield |
| With triethylsilane; boron trifluoride diethyl etherate In 1,2-dichloro-ethane; acetonitrile at 0 – 50℃; for 3h; Experimental Procedure 12 4.12. 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene (15) Et3SiH (6.76 mL, 42.34 mmol) was added to a solution of compound 14 (6.0 g, 17.8 mmol) in 1:2 mixture of dry 1,2-dichloroethane/acetonitrile (2:1, 60 mL) and the mixture was cooled in an ice bath. BF3·OEt2 (2.53 mL, 20.51 mmol) was added and the mixture was heated at 50 °C for 3 h and then cooled at room temperature. Aqueous 7N KOH (30 mL) was added and the aqueous layer was extracted with dichloromethane (2 * 100 mL). The combined organic layers were washed with 2N KOH (2*) and brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was chromatographed on a silica gel column (hexane/ethyl acetate 15:1) to give product 15 (5.6 g, 97%) as colorless crystals, with spectral and physical data identical to those reported in the literature [7], m.p. 40-42 °C (lit. m.p. 37 °C and 40-41 °C). 1H NMR (400 MHz, CDCl3) 7.20-7.28 (m, 3H), 7.08 (d, J = 8.8, 2H), 6.83 (d, J = 8.8, 2H), 4.00 (q, J = 7.0, 2H), 3.96 (s, 2H), 1.40 (t, J = 7.0, 3H); 13C NMR (125 MHz, CDCl3) 157.6, 141.3, 133.5, 133.1, 130.9, 130.5, 130.4, 130.0, 120.4, 114.6, 63.4, 38.2, 14.9. LC-MS (ESI positive) m/z: 325 [M+H]+. | 97% |
| Stage #1: (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone With sodium tetrahydroborate In dichloromethane; acetonitrile at 30 – 40℃; for 0.5h; Stage #2: With chloro-trimethyl-silane In dichloromethane; acetonitrile at 30 – 40℃; for 3h; Stage #3: With boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 – 35℃; for 8h; Inert atmosphere; Experimental Procedure 3 Example 3 Synthesis of 4-bromo-1-chloro-2- (4-ethoxybenzyl) benzene Under nitrogen, 1 g of (5-bromo-2-chlorophenyl) – (4-ethoxyphenyl) methanone and10.88g dichloromethane was added to 100mL reaction flask, warmed to 30-40 ° C, added 2.88g acetonitrile, 0.22g sodium borohydride, stirred at 30-40 ° C for 0.5h, 0.96g trimethylchlorosilane was added dropwise, after dripping 30-40 for 3hrs, cooled to 0-5 , 0.63g of boron trifluoride diethyl ether was slowly added dropwise, the temperature was controlled <10 , after warming to 30-35 after dropping for 4hrs, cooled to 10-15 ° C, add 0.22g of sodium borohydride, 0.63g of boron trifluoride diethyl ether, the temperature was raised to 30-35 ° C reaction 4hrs, cooled to 0-5 ° C, 20mL methylene chloride was added slowly dropwise 20mL 12% sodium carbonate solution , Continue stirring after dropping 20mins, the layers were separated, the aqueous phase was extracted twice with 40mL of methylene chloride, the combined organic phases were washed once with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.92g slightly yellow solid, yield 96%. | 96% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Danger |
| GHS Hazard Statements | H302 (13.33%): Harmful if swallowed [Warning Acute toxicity, oral] H312 (11.11%): Harmful in contact with skin [Warning Acute toxicity, dermal] H318 (84.44%): Causes serious eye damage [Danger Serious eye damage/eye irritation] H332 (11.11%): Harmful if inhaled [Warning Acute toxicity, inhalation] H400 (84.44%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard] H410 (84.44%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard] |
| Precautionary Statement Codes | P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P321, P330, P362+P364, P391, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| HS Code | |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 325.633 |
| logP | 5.535 |
| HBA | 0 |
| HBD | 0 |
| Matching Lipinski Rules | 3 |
| Veber rules component | |
| Polar Surface Area (PSA) | 9.23 |
| Rotatable Bond (RotB) | 4 |
| Matching Veber Rules | 2 |
| Use Pattern |
| 5-bromo-2-chloro-4¡¯-ethoxydiphenylmethane CAS 461432-23-5 is used as a synthetic reagent for the production of dapagliflozin, an effective and selective sodium-glucose co-transporter 2 (SGLT2) inhibitor used in the treatment of type 2 diabetes. |
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