Sodium Methoxide → {2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]phenyl}methanol

HRID 1873471Notes

Reaction equation

HRID 1873471 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:13][C:14]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[CH2:15][N:16]=2)=[CH:8][C:7]=1[Br:29])(=O)C.C[O-].[Na+]>CO.COC(C)(C)C>[Br:29][C:7]1[CH:8]=[C:9]([C:12]2[CH2:13][C:14]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:18])([F:19])[F:20])[CH2:15][N:16]=2)[CH:10]=[CH:11][C:6]=1[CH2:5][OH:4]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 580920762-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzyl acetate

Product 1

HCID 58092103{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]phenyl}methanolYield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzyl acetate (1.1 g) in methanol (20 ml) was added sodium methoxide (0.1 g), and the solution was stirred for 1 hour at room temperature. The reaction mixture was returned to room temperature and then diluted with t-butyl methyl ether, washed with water and a saturated aqueous brine and subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain {2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]phenyl}methanol (0.95 g).

Workup

  1. customwas returned to room temperature
  2. washwashed with water
  3. dry with materiala saturated aqueous brine and subsequently dried over magnesium sulfate
  4. filtrationAfter filtering the reaction mixture
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-70400085bd8549a5950e499522ae1237
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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