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

HRID 1899074노트

반응식

HRID 1899074 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5c4183304c0e4bfcb4c7037a3fc4612b
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05571810

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