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Tetrabutylammonium Fluoride Trihydrate → 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-methyl-3,4-dihydro-2H-pyrrole

HRID 1844642
Notes
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Reaction equation

HRID 1844642 reaction equation
CS[C:3](=[N:12][CH2:13][Si](C)(C)C)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([Cl:11])[CH:5]=1.[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([C:27](F)(F)F)=[CH2:26])[CH:22]=[C:21]([Cl:31])[CH:20]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]2[CH2:27][C:25]([C:23]3[CH:22]=[C:21]([Cl:31])[CH:20]=[C:19]([Cl:18])[CH:24]=3)([CH3:26])[CH2:13][N:12]=2)=[CH:5][C:6]=1[Cl:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 668366594-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

Product 1

HCID 675066625-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-methyl-3,4-dihydro-2H-pyrroleYield 114.8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (Example I14) (1.83 g) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (see WO 2007125984) (1.38 g) in THF (25 ml) was added at −5° C. tetrabutylammonium fluoride trihydrate (TBAF) (0.41 g) dissolved in THF (15 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture concentrated and the residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:6) to give 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-methyl-3,4-dihydro-2H-pyrrole (2.50 g). 1H-NMR (400 MHz, CDCl3): 7.95-7.25 (m, 6H), 4.88 (d, 1H), 4.42 (d, 1H), 3.75 (d, 1H), 3.40 (d, 1H) ppm.

Workup

  1. customwas added at −5° C.
  2. concentrationThe reaction mixture concentrated
  3. customthe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:6)

Sources & evidence

ORD record
ord-0afb244090c744bd8ce0752813c79262
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946447B2

Reaction notes

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