Boron tribromide → 6-Isoquinolinol, 7-bromo-

HRID 1022853Notes

Reaction equation

HRID 1022853 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][N:12]=[CH:13]2)=[CH:8][C:7]=1[O:16]C.C([O-])(O)=O.[Na+]>ClCCl>[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][N:12]=[CH:13]2)=[CH:8][C:7]=1[OH:16]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 230784917-Bromo-6-methoxyisoquinoline

Product 1

HCID 1358548376-Isoquinolinol, 7-bromo-Yield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.6 mL (9.5 g, 37.8 mmol) of BBr3 were added at 0° C. to a solution of 4.5 g (18.9 mmol) 7-bromo-6-methoxy isoquinoline in 30 mL dichloromethane and stirred for 18 h at room temperature. Aqueous NaHCO3-solution was added to adjust the pH to 8. Extraction with chloroform/isopropanol (3/1) followed by drying over sodium sulfate and removal of the solvents gave 2.7 g (64%) of compound 1.

Workup

  1. extractionExtraction with chloroform/isopropanol (3/1)
  2. dry with materialby drying over sodium sulfate and removal of the solvents

Sources & evidence

ORD record
ord-36336b1f0b0d4d2a97fcb40876c09499
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

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