2-Bromothiophene → HCID 86078978、化合物

HRID 490857

反応式

HRID 490857 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 86078978HCID 86078978、化合物収率 33.3%

試薬・触媒・溶媒 1

HCID 6348Carbon Disulfide溶媒

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-3755f55c2b0f42b1aaa99adce2ebf18f
出典データセット
uspto-grants-2009_05
特許番号
US07528176B2

関連ノート

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