IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product Name5-bromo-2-chloro-4’-ethoxydiphenylmethane IUPAC Name4-bromo-1-chloro-2-benzeneMolecular StructureCAS Registry Number 461432-23-5MDL NumberMFCD11042292Synonyms461432-23-54-bromo-1-chloro-2-(4-ethoxybenzyl)benzene4-(5-Bromo-2-chlorobenzyl)phenyl ethyl ether5-Bromo-2-chloro-4'-ethoxydiphenylmethane4-bromo-1-chloro-2-benzeneBenzene, 4-bromo-1-chloro-2--MFCD110422922-(4-ethoxybenzyl)-4-bromo-1-chlorobenzeneC15H14BrClO4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene; 4-bromo-1-chloro-2-benzene5-bromo-2-chloro-4 inverted exclamation mark -ethoxydiphenylmethaneSCHEMBL38150DTXSID60433931ZUNCHZBITMUSRD-UHFFFAOYSA-NBCP08717CS-B0023AKOS015917373SB17549AC-26384DS-12747SY025637AM200405244-bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methaneEN300-6735475A8499024-bromo-1-chloro-2-(4-ethoxyphenyl)methyl-benzene4-BROMO-1-CHLORO-2--BENZENEMolecular FormulaC15H14BrClOMolecular Weight325.63InChIInChI=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,2,9H2,1H3InChI KeyZUNCHZBITMUSRD-UHFFFAOYSA-N Isomeric SMILESCCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)Br)Cl
Patent InformationPatent IDTitlePublication DateCN117551153,A method for the synthesis of dapagliflozin intermediates by continuous reaction2024CN115785045Photocatalytic Endagliflozin precursor and synthesis method thereof2023CN116120299Preparation method of 1-C-substituted phenyl glucopyranose carbon glycoside2023CN116789716Preparation method of dapagliflozin and etogliflozin intermediates2023
Physical Data
AppearanceWhite to off -white solid powder
Melting Point, °C Solvent (Melting Point) 40 - 41ethanol40 - 4242 - 4538 - 4039 - 4140 - 4137ethanol
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts, Spectrum1Hchloroform-d1Chemical shifts, Spectrum13Cchloroform-d1Chemical shifts1Hchloroform-d1Chemical shifts, Spectrum1Hchloroform-d1400
Route of Synthesis (ROS)
Route of Synthesis (ROS) of 5-bromo-2-chloro-4¡¯-ethoxydiphenylmethane CAS 461432-23-5
ConditionsYieldWith triethylsilane; boron trifluoride diethyl etherate In 1,2-dichloro-ethane; acetonitrile at 0 - 50℃; for 3h;Experimental Procedure12 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 , 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 +.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 Procedure3 Example 3 Synthesis of 4-bromo-1-chloro-2- (4-ethoxybenzyl) benzeneUnder 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
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