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

HRID 1926666Notes

Reaction equation

HRID 1926666 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-36d763a866894331b91e0dc272c4b8e5
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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