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

HRID 1852221ノート

反応式

HRID 1852221 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 717427161-Chloro-7-fluoroisoquinolin-4-OL収率 93%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b01971e8b3ea4317b52aacaed5bbd159
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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