Sodium borohydride → (3,5-Bis-trifluoromethylphenyl)(3-methyl-4-nitrophenyl)methanol

HRID 1640100Notes

Reaction equation

HRID 1640100 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:28])([F:27])[C:5]1[CH:6]=[C:7]([C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>CO.C(OCC)(=O)C>[F:3][C:4]([F:27])([F:28])[C:5]1[CH:6]=[C:7]([CH:15]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)[OH:26])[CH:8]=[C:9]([C:11]([F:13])([F:12])[F:14])[CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 219403763',5'-Bis-trifluoromethyl-3-methyl-4-nitrobenzophenone

Product 1

HCID 59229512(3,5-Bis-trifluoromethylphenyl)(3-methyl-4-nitrophenyl)methanolYield 72.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (0.12 g) was added to a solution of 3′,5′-bis-trifluoromethyl-3-methyl-4-nitrobenzophenone (2.2 g) in methanol (10 ml) in an ice bath. After stirring at room temperature for 1 hour, and diluting with ethyl acetate, it was washed with water and a saturated salt solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off and the residue was purified by silica gel column chromatography to obtain (3,5-bis-trifluoromethylphenyl)(3-methyl-4-nitrophenyl)methanol (1.6 g).

Workup

  1. washwas washed with water
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4fec940c226447438cfb22d7bcd8c73e
Source dataset
uspto-grants-2012_02
Patent number
US08110689B2

Reaction notes

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