Benzeneacetyl chloride, 4-bromo- → HCID 57441117、化合物

HRID 133429

反応式

HRID 133429 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[Si](C)(C)C.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](Cl)=[O:23])=[CH:17][CH:16]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:22](=[O:23])[CH2:21][C:18]1[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][CH:17]=1

参加物

5

反応物 2

HCID 181552Benzeneacetyl chloride, 4-bromo-HCID 13148489HCID 13148489、化合物

生成物 1

HCID 57441117HCID 57441117、化合物収率 17.4%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

Benzofuran-2-yl-trimethyl-silane (3.4 g, 17.86 mmol) was dissolved in methylene chloride (40 mL) and cool to −78° C. 4-Bromophenyl-acetyl chloride (19.65 mmol, 1.1 equiv.) was added at this temperature. Under vigorous stirring, a solution of TiCl4 (23 mL, 1M, 23.2 mmol, 1.3 equiv.) in CH2Cl2 was added dropwise and stirring continued for 20 min. Then the reaction was quenched with H2O (100 mL), cooling bath was removed and the mixture was allowed to warm up to room temperature. It was then diluted with H2O (100 mL) and extracted with CH2Cl2 (3×). Organic layers were combined, washed with brine, dried over MgSO4, solvent evaporated. Crude product thus obtained was subject to column purification. (silica gel, 10% EtOAC/Hexane). 980 mg of 1-Benzofuran-2-yl-2-(4-bromo-phenyl)-ethanone was obtained in 17% yield.

後処理

  1. customThen the reaction was quenched with H2O (100 mL)
  2. temperaturecooling bath
  3. customwas removed
  4. temperatureto warm up to room temperature
  5. additionIt was then diluted with H2O (100 mL)
  6. extractionextracted with CH2Cl2 (3×)
  7. washwashed with brine
  8. dry with materialdried over MgSO4, solvent
  9. customevaporated
  10. customCrude product thus obtained
  11. customwas subject to column purification

出典と根拠

ORDレコード
ord-bd8690d6e4de443b9130f9f4ec584821
出典データセット
uspto-grants-2008_06
特許番号
US07390833B2

関連ノート

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