Water → [3-(4-Bromo-2-hydroxymethyl-phenoxy)-phenyl]-acetic acid methyl ester

HRID 885248Notes

Reaction equation

HRID 885248 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH:19]=[O:20])[CH:6]=1.[BH4-].[Na+].O.CCOC(C)=O>CO>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][OH:20])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 58237467[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester

Product 1

HCID 58237523[3-(4-Bromo-2-hydroxymethyl-phenoxy)-phenyl]-acetic acid methyl esterYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To [3-(4-bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester (4.8 g, 13.7 mmol) in MeOH (50 mL) was added sodium borohydride (0.78 g, 20.6 mmol), and the reaction was stirred at room temperature for 5 minutes. The mixture was worked-up with H2O and EtOAc, and the crude material was purified by silica gel chromatography to give the desired product as a colorless oil (3 g).

Workup

  1. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9e28d60c37324cdab4dd093d930ddfe6
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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