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

HRID 1247451노트

반응식

HRID 1247451 반응식
[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]

참가 물질

4

반응물 2

HCID 25134Boron tribromide2회HCID 219075434-Bromo-6-methoxy-2,3-dihydro-1H-isoindol-1-one

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-e133d9d73ecd47e898303bac7b3c48b2
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129260B2

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