Boron tribromide → HCID 86683273, compound

HRID 1852262Notes

Reaction equation

HRID 1852262 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][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](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71742711HCID 71742711, compound

Product 1

HCID 86683273HCID 86683273, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,5-dichloro-4-methoxyisoquinoline (1.2 g, 5.26 mmol) in DCM (15 ml) was added BBr3 (9.23 g, 34.8 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 (0.7 g, 62.2%) as light brown color solid. 1H NMR (400 MHz, CD3OD): δ ppm 8.28-8.25 (d, J=12 Hz, 1H), 7.85-7.82 (m, 2H), 7.68-7.64 (m, 1H); MS: MS m/z 214.0 (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-659819c1c2ef4b6d9afdcd9b89cd6501
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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