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

HRID 1852218Notes

Reaction equation

HRID 1852218 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 a 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).

Workup

  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

Sources & evidence

ORD record
ord-160f48e4fea6431fb1b19894e3a53384
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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