Sodium borohydride → N-[4-(2-bromo-1-hydroxyethyl)phenyl]acetamide

HRID 23693

Reaction equation

HRID 23693 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>C(OCC)C.O>[Br:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 12364739N-[4-(2-Bromoacetyl)Phenyl]Acetamide

Product 1

HCID 22563212N-[4-(2-bromo-1-hydroxyethyl)phenyl]acetamideYield 18.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-[4-(2-bromoacetyl)phenyl]acetamide (2.1 g, 0.0082 mol, in 30 mL of methanol) was introduced solid NaBH4 (1.0 g, 0.026 mol) at 0° C. and stirred at that temperature for 15 minutes. The mixture was diluted with diethyl ether (20 mL) and water (20 mL). The ether phase was separated and the aqueous phase was extracted with diethyl ether. The ether phases were combined and washed with brine, dried. Purification on a silica gel column gave the title compound as a white solid (0.40 g).

Workup

  1. customThe ether phase was separated
  2. extractionthe aqueous phase was extracted with diethyl ether
  3. washwashed with brine
  4. customdried
  5. customPurification on a silica gel column

Sources & evidence

ORD record
ord-8ad6315898104647b2eb53bf2349ec6b
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

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