Boron tribromide → 4-Bromo-6-hydroxy-2,3-dihydro-1H-isoindol-1-one

HRID 1247451ノート

反応式

HRID 1247451 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([O:11]C)[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13]

参加物

4

反応物 2

HCID 25134Boron tribromide2 回HCID 219075434-Bromo-6-methoxy-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 219075354-Bromo-6-hydroxy-2,3-dihydro-1H-isoindol-1-one収率 97.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

A −78° C. suspension of Example 104A (100 mg, 0.41 mmol) in dichloromethane (13 mL) was treated dropwise with 1M BBr3 in dichloromethane (1.2 mL, 1.2 mmol), stirred at −78° C. for 1 hour, and stirred at room temperature for 2 hours. The mixture was treated with additional 1M BBr3 in dichloromethnae (0.8 mL), heated to reflux overnight, then cooled to room temperature, and partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4), filtered, and concentrated to give 91 mg (97%) of the desired product. MS (ESI(−)) m/226, 228 (M−H)−.

後処理

  1. stirringstirred at room temperature for 2 hours
  2. temperatureheated
  3. temperatureto reflux overnight
  4. temperaturecooled to room temperature
  5. custompartitioned between water and ethyl acetate
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-e133d9d73ecd47e898303bac7b3c48b2
出典データセット
uspto-grants-2006_10
特許番号
US07129260B2

反応ノート

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