Tetrabutylammonium Fluoride → 2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzyl acetate

HRID 1873470Notes

Reaction equation

HRID 1873470 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](SC)=[N:13][CH2:14][Si](C)(C)C)=[CH:8][C:7]=1[Br:21])(=[O:3])[CH3:2].[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([C:31]([F:34])([F:33])[F:32])=[CH2:30])[CH:26]=[C:25]([Cl:35])[CH:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.COC(C)(C)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:30][C:29]([C:27]3[CH:26]=[C:25]([Cl:35])[CH:24]=[C:23]([Cl:22])[CH:28]=3)([C:31]([F:32])([F:34])[F:33])[CH2:14][N:13]=2)=[CH:8][C:7]=1[Br:21])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 668200202-Bromo-4-[(methylsulfanyl){[(trimethysilyl)methyl]imino}methyl]benzyl acetate

Product 1

HCID 580920762-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzyl acetateYield 93.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Under argon atmosphere, a mixed solution of 2-bromo-4-[(methylsulfanyl){[(trimethysilyl)methyl]imino}methyl]benzyl acetate (0.90 g) and 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (0.56 g) in THF was cooled to −5° C. to be stirred, and a solution of tetrabutylammonium fluoride (0.56 ml, of 1.0 M in THF) was added thereto gradually. The reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was diluted with t-butyl methyl ether and washed with water and a saturated aqueous brine, 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]benzyl acetate (1.1 g).

Workup

  1. stirringThe reaction mixture was stirred for 20 hours at room temperature
  2. washwashed with water
  3. dry with materiala saturated aqueous brine, 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-828e9f7c8a9a400c849c8ef7015b337b
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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