Bromobenzene → 1-Phenyl-2-(thiophen-3-yl)ethanone

HRID 924656노트

반응식

HRID 924656 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.CON(C)[C:16](=[O:23])[CH2:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1>[C:2]1([C:16](=[O:23])[CH2:17][C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 11423995N-methoxy-N-methyl-2-(thiophen-3-yl)acetamideHCID 178418339Butyllithium

생성물 1

HCID 122331131-Phenyl-2-(thiophen-3-yl)ethanone수율 55%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To the solution of bromo-benzene (1.0 g, 6.36 mmol) in anhydrous THF (30 mL) was added n-BuLi (5.9 mmol, 2.4 mL) at −78° C. under nitrogen, and the mixture was stirred at −78° C. for further 20 min., a solution of N-methoxy-N-methyl-2-(thiophen-3-yl)acetamide (1 g, 5.4 mmol) in anhydrous THF (10 mL) was added. The resulting mixture was stirred at −78° C. under nitrogen for about 30 min., poured into NH4Cl aqueous solution, and extracted with EtOAc. The organic layers were washed with brine, dried over sodium sulfate, concentrated, and purified by column chromatography (PE:EtOAc=20:1) to afford Intermediate 6 (600 mg, yield 55.0%).

후처리

  1. stirringThe resulting mixture was stirred at −78° C. under nitrogen for about 30 min.
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (PE:EtOAc=20:1)

출처 및 근거

ORD 기록
ord-912493bb11264607966fbb3a89ec49df
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283213B2

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