Sodium borohydride → [3-(4-Bromo-2-hydroxymethyl-phenoxy)-phenyl]-acetic acid ethyl ester

HRID 885234Notes

Reaction equation

HRID 885234 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[CH:20]=[O:21])[CH:7]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[CH2:20][OH:21])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58237452[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid ethyl ester

Product 1

HCID 58237503[3-(4-Bromo-2-hydroxymethyl-phenoxy)-phenyl]-acetic acid ethyl esterYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To [3-(4-bromo-2-formyl-phenoxy)-phenyl]-acetic acid ethyl ester (0.70 g, 1.9 mmol) in MeOH (20 mL) was added sodium borohydride (0.07 g, 1.9 mmol), and the reaction was stirred for 5 minutes at room temperature. Once no starting material was seen by analytical tlc, the mixture was worked-up to give the desired product (0.7 g).

Sources & evidence

ORD record
ord-695d6a9b6af849759a98920607090aec
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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