Tetrabutylammonium Fluoride → 5-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole

HRID 241513ノート

反応式

HRID 241513 の反応式
CS[C:3](=[N:12][CH2:13][Si](C)(C)C)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[CH:5]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:26](=[CH2:31])[C:27]([F:30])([F:29])[F:28])[CH:22]=[C:23]([Cl:25])[CH:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]2[CH2:31][C:26]([C:21]3[CH:22]=[C:23]([Cl:25])[CH:24]=[C:19]([Cl:18])[CH:20]=3)([C:27]([F:28])([F:30])[F:29])[CH2:13][N:12]=2)=[CH:5][C:6]=1[CH3:11]

参加物

5

反応物 3

HCID 2724141Tetrabutylammonium FluorideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 668366694-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

生成物 1

HCID 866910465-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (4.40 g, 13.3 mmol) in dry THF (60 mL) was added 2-(3,5-dichlorophenyl)-1,1,1-trifluoro-2-propene (4.35 g, 16.25 mmol) at −7° C. A solution of tetrabutyl ammoniumfluoride (5.32 mL, 1 M in THF, 5.33 mmol) was added at this temperature and the mixture was allowed to warm to room temperature over night. All volatiles were removed in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (4.50 g, 75%).

後処理

  1. customAll volatiles were removed in vacuum
  2. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-008647fd4d7447f2a5e3f27bf0253311
出典データセット
uspto-grants-2014_02
特許番号
US08653000B2

反応ノート

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