Sodium borohydride → 1-(2-Amino-5-bromophenyl)ethan-1-ol

HRID 1816883Notes

Reaction equation

HRID 1816883 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([OH:11])[CH3:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 110747461-(2-Amino-5-bromophenyl)ethan-1-one

Product 1

HCID 688650521-(2-Amino-5-bromophenyl)ethan-1-olYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-amino-5-bromo-phenyl)-ethanone (2.4 g, 11.2 mmol) in anhydrous methanol (50 mL) was added sodium borohydride (1 g, 26 mmol) at rt under nitrogen. The mixture was stirred for 1 h, poured onto ice water, and extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (MgSO4) and concentrated to yield the title compound as an off-white solid (2.1 g, 86%): mp 95-96° C.

Workup

  1. additionpoured onto ice water
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9d1b461a07f48289a4ceca529ce69c5
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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