5-Bromo-2-chlorobenzoyl chloride → 1-[6-(5-Bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

HRID 72565

反応式

HRID 72565 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:3][CH2:2]1.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23](Cl)=[O:24].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:27])=[C:22]([CH:26]=1)[C:23]([C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][N:4]([C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])[C:5]=2[CH:10]=1)=[O:24]

参加物

5

反応物 3

HCID 27568715-Bromo-2-chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15171868HCID 15171868、化合物

生成物 1

HCID 866551971-[6-(5-Bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone収率 79.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 1-(2,3-dihydro-benzo[1,4]oxazin-4-yl)-2,2,2-trifluoro-ethanone (6.5 g, 28.1 mmol) in dichloromethane (45 mL) was added 5-bromo-2-chlorobenzoyl chloride (8.54 g, 33.7 mmol) in dichloromethane (35 mL) and AlCl3 (5.61 g, 42.2 mmol) at 0° C. After 2 h, the reaction mixture was brought to room temperature and stirred overnight. The reaction was quenched by pouring over crushed ice and extracted with dichloromethane (2×50 mL). The organic layer was washed with aq. NaHCO3 (30 mL), H2O (20 mL), and the solvent evaporated to get the crude product which was purified by silica gel column chromatography to give 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (10.0 g).

後処理

  1. customwas brought to room temperature
  2. customThe reaction was quenched
  3. additionby pouring
  4. customover crushed ice
  5. extractionextracted with dichloromethane (2×50 mL)
  6. washThe organic layer was washed with aq. NaHCO3 (30 mL), H2O (20 mL)
  7. customthe solvent evaporated
  8. customto get the crude product which
  9. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9e8d94565faf43948f9b5faeb25898aa
出典データセット
uspto-grants-2014_09
特許番号
US08828951B2

関連ノート

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