Phosphorus oxybromide → 2-Bromo-6-methoxyquinoline

HRID 2045715노트

반응식

HRID 2045715 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[CH:6]2.P(Br)(Br)([Br:16])=O>>[Br:16][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

참가 물질

3

반응물 2

HCID 24613Phosphorus oxybromideHCID 2282682-Hydroxy-6-methoxyquinoline

생성물 1

HCID 114704222-Bromo-6-methoxyquinoline수율 49.3%

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온도
140 °C

실험 절차

6-Methoxyquinolin-2(1H)-one (6.81 g, 38.9 mmol) was carefully added to POBr3 (18.9 g, 66.1 mmol) at 60° C., and the resulting solution was stirred at 140° C. for 2.5 h. The reaction mixture was cooled and poured onto crushed ice, and the solid was collected by filtration. Purification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether) afforded the title compound (4.57 g, 49.3%) as a solid. LCMS (ES+) m/z 238, 240 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationthe solid was collected by filtration
  5. customPurification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-9042e30c9dd44a0ea7cfddb3ec75d3e9
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591878B2

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