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

HRID 924656ノート

反応式

HRID 924656 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-912493bb11264607966fbb3a89ec49df
出典データセット
uspto-grants-2016_03
特許番号
US09283213B2

反応ノート

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