Sodium borohydride → 1-(4'-Bromobiphenyl-4-yl)propan-2-ol

HRID 1626790Notes

Reaction equation

HRID 1626790 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([OH:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68193283(4'-Bromobiphenyl-4-yl)acetone

Product 1

HCID 681932011-(4'-Bromobiphenyl-4-yl)propan-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4′-Bromobiphenyl-4-yl)acetone (7.6 g, 26 mmol) was dissolved in ethanol (250 mL), and sodium borohydride (1.2 g, 32 mmol) was added at 0° C., followed by stirring at the same temperature for 30 minutes. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the resulting residue, and the organic layer was washed with water. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.45 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (7.6 g, 26 mmol) as a white solid (yield 99%).

Workup

  1. concentrationAfter the reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the resulting residue
  3. washthe organic layer was washed with water
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  6. concentrationa fraction corresponding to the Rf value=0.45 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c768dc6c94d488f8ea5fab14a0acdf7
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

Loading…