3-Bromobenzophenone → (3-Bromophenyl)(phenyl)methanol

HRID 1027448

Reaction equation

HRID 1027448 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[BH4-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[OH:6])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 705483-BromobenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 285827(3-Bromophenyl)(phenyl)methanolYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-bromobenzophenone (1.00 g, 4 mmol) in MeOH (15 mL) was added sodium borohydride (0.3 mL, 8 mmol) portionwise at rt and the suspension was stirred at rt for 1-24 h. The reaction was diluted slowly with water and extracted with CH2Cl2. The organic layer was washed successively with water, brine, dried over Na2SO4, and concentrated to give the title compound as oil (0.8 g, 79%), which was used in the next reaction without further purification. MS (ESI, pos. ion) m/z: 247.1 (M-OH).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed successively with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d410541761445d0900f5484df9ca106
Source dataset
uspto-grants-2014_05
Patent number
US08735383B2

Linked notes

Loading…