Boron tribromide → 1-Chloro-7-fluoroisoquinolin-4-OL

HRID 1852221노트

반응식

HRID 1852221 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([O:13]C)=[CH:4][N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 222502381-Chloro-7-fluoro-4-methoxyisoquinoline

생성물 1

HCID 717427161-Chloro-7-fluoroisoquinolin-4-OL수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1-chloro-7-fluoro-4-methoxyisoquinoline (0.75 g, 3.54 mmol) in DCM (10 ml) was added BBr3 (6.22 g, 24.81 mmol) at 0° C. drop wise. The reaction mass was refluxed for 5 h. The residue was cooled and quenched with methanol. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The precipitated solid was filtered, washed with water to get crude compound (0.65 g, 93%) as pale yellow solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.36-8.33 (m, 1H), 7.89-7.86 (d, J=12 Hz, 1H), 7.76 (s, 1H), 7.64 (t, J=10 Hz, 1H); MS: MS m/z 198.0 (M++1).

후처리

  1. temperatureThe reaction mass was refluxed for 5 h
  2. temperatureThe residue was cooled
  3. customquenched with methanol
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe residue was diluted with cold water
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water

출처 및 근거

ORD 기록
ord-b01971e8b3ea4317b52aacaed5bbd159
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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