Hydrochloric Acid → 2-(4-Fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)thiophene

HRID 1899074ノート

反応式

HRID 1899074 の反応式
Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[CH:3]=1.[F:24][C:25]([F:30])([F:29])C([O-])=O.[Na+].ClCCl.Cl>CN(C)C(=O)C.O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[S:6][C:2]([C:25]([F:30])([F:29])[F:24])=[CH:3][C:4]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 31775-Bromo-2-(4-fluorophenyl)-3-(4-(methylsulfonyl)phenyl)thiopheneHCID 6344DichloromethaneHCID 517019Sodium Trifluoroacetate

生成物 1

HCID 99308472-(4-Fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)thiophene収率 14.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A mixture of 5-bromo-2-(4-fluorophenyl)-3-[4(methylsulfonyl)phenyl]thiophene (7.2 g), sodium trifluoroacetate (9.4 g) and cuprous iodide (6.5 g) in N,N-dimethylacetamide (109 ml), was stirred and refluxed for 5 hours. Dichloromethane (200 ml), 3N hydrochloric acid (100 ml) and water (100 ml) were added to the reaction mixture. The resulting mixture was filtered, and the filtrate was separated. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue (13.9 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (50:1). The crude product (1.3 g) was recrystallized from ethanol to give pale brown crystal of 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)thiophene (1.04 g).

後処理

  1. temperaturerefluxed for 5 hours
  2. filtrationThe resulting mixture was filtered
  3. customthe filtrate was separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue (13.9 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (50:1)
  8. customThe crude product (1.3 g) was recrystallized from ethanol

出典と根拠

ORDレコード
ord-5c4183304c0e4bfcb4c7037a3fc4612b
出典データセット
uspto-grants-1996_11
特許番号
US05571810

反応ノート

読み込み中…