Boron tribromide → 3-tert-butyl-6-hydroxy-2-methyl-4-phenylisoquinolin-1(2H)-one

HRID 2196382Notes

Reaction equation

HRID 2196382 reaction equation
[C:1]([C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21]C)=[CH:10][CH:9]=2)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([OH:21])=[CH:10][CH:9]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 685091933-tert-butyl-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

Product 1

HCID 112782303-tert-butyl-6-hydroxy-2-methyl-4-phenylisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (5 mL) solution of 3-tert-butyl-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (100 mg, 0.311 mmol) under argon at −70 C was added boron tribromide (1.0M, 0.934 mL, 0.934 mmol). The contents of the reaction flask were warmed to room temperature and stirred 24 h. Extracted with methylene chloride (3×), then the combined organic extracts were washed with brine and dried with anhydrous sodium sulfate. Filtration followed by evaporation of solvent in vacuo gave a solid which was triturated with ethanol. Recrystallization from ethyl acetate/ethanol afforded the title compound.

Workup

  1. extractionExtracted with methylene chloride (3×)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationFiltration
  5. customfollowed by evaporation of solvent in vacuo
  6. customgave a solid which
  7. customwas triturated with ethanol
  8. customRecrystallization from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-ae2339bbfa844f64909d2dddfcc2ed2f
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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