Sodium borohydride → 1-(4-Bromophenyl)butan-2-ol

HRID 735683Notes

Reaction equation

HRID 735683 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:12])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([OH:12])[CH2:10][CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 154196931-(4-Bromophenyl)butan-2-one

Product 1

HCID 578426191-(4-Bromophenyl)butan-2-olYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 70B (478 mg, 2.1 mmol) in 5 mL MeOH at 0° C., was added NaBH4 (110 mg, 2.98 mmol). The solution was stirred at rt for 30 min, then was diluted with EtOAc and washed with H2O and brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70C (460 mg, 96%). MS (ESI) m/z 221.2 (M-OH)+.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification via flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d4fa01af1dda438c93d87216ef8a2f6e
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…