2-Bromothiophene → HCID 86078978, 화합물

HRID 490857

반응식

HRID 490857 반응식
[F:1][C:2]1[C:10]([F:11])=[C:9](F)[C:8]([F:13])=[C:7]([F:14])[C:3]=1[C:4](Cl)=[O:5].[Br:15][C:16]1[S:17][CH:18]=[CH:19][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[F:14][C:7]1[C:8]([F:13])=[CH:9][C:10]([F:11])=[C:2]([F:1])[C:3]=1[C:4]([C:18]1[S:17][C:16]([Br:15])=[CH:20][CH:19]=1)=[O:5]

참가 물질

5

반응물 3

HCID 138512-BromothiopheneHCID 75256Pentafluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 86078978HCID 86078978, 화합물수율 33.3%

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

To a mixture of perfluorobenzoyl chloride (2.51 g, 10.9 mmol) and 2-bromothiophene (1.86 g, 11.4 mmol) in carbon disulfide (80 mL), aluminum chloride (2.90 g, 21.8 mmol) was added in portions over 10 min with vigorous mechanical stirring. The reaction mixture turned red and was stirred for 2.5 h before being quenched with water (80 mL). The organics were then separated, the aqueous layer extracted with carbon disulfide (3×50 mL), and the combined organics washed with water (3×100 mL) and dried over MgSO4. After filtration, the organics were concentrated in vacuo and the chromatographed on a silica gel column (hexane:ether=9:1) to yield 1.23 g (32%) green crystals. mp 51-54° C.; 1H NMR (DMSO): δ 7.78 (d, 2H, 3J=3.6 Hz), 7.54 (d, 2H, 3J=4.4 Hz); 19F NMR (DMSO): δ −142.1 (m, 2H), −151.6 (m, 1H), −160.6 (m, 2H) Anal. Calcd for C11H2BrF5OS: C 37.00, H 0.56. Found: C 37.37, H 0.83; MS (EI): m/z (%) 355.8 (92) [M+].

후처리

  1. additionwas added in portions over 10 min with vigorous mechanical stirring
  2. custombefore being quenched with water (80 mL)
  3. customThe organics were then separated
  4. extractionthe aqueous layer extracted with carbon disulfide (3×50 mL)
  5. washthe combined organics washed with water (3×100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe organics were concentrated in vacuo
  9. customthe chromatographed on a silica gel column (hexane:ether=9:1)

출처 및 근거

ORD 기록
ord-3755f55c2b0f42b1aaa99adce2ebf18f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528176B2

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