Water → 6-Fluoro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 577448Notes

Reaction equation

HRID 577448 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[C:8](=[O:14])[NH:7][CH2:6][CH2:5]2.B(Br)(Br)Br.O.CCOC(C)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[C:8](=[O:14])[NH:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 867236856-fluoro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 575676666-Fluoro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 6-fluoro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (Cpd M, 0.428 g, 2.19 mmol) in DCM (15 mL) was added boron tribromide (1.0M in DCM, 6.00 mL, 6.00 mmol). The reaction mixture was stirred for 1 hour, then the reaction mixture was allowed to warm to room temperature. After stirring for 4 hours, water (25 mL) and EtOAc (100 mL) were added and the mixture was stirred vigorously. The layers were separated, and the organic layer was filtered and concentrated under vacuum to give 6-fluoro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (Cpd N, 355 mg, 89%).

Workup

  1. stirringAfter stirring for 4 hours
  2. stirringthe mixture was stirred vigorously
  3. customThe layers were separated
  4. filtrationthe organic layer was filtered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-795a15b2a98f47dbae2a664056b1beb2
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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