Benzeneacetyl chloride, 4-bromo- → HCID 57441117, 화합물

HRID 915781

반응식

HRID 915781 반응식
[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

참가 물질

5

반응물 2

HCID 181552Benzeneacetyl chloride, 4-bromo-HCID 131484892-(Trimethylsilyl)benzofuran

생성물 1

HCID 57441117HCID 57441117, 화합물수율 17.4%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cee734425971457484f01b14cf5b83bc
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268135B2

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