Bromine → 4-Bromo-6-fluoro-2-methylisoquinolin-1-one

HRID 518283Notes

Reaction equation

HRID 518283 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([CH3:15])[CH:8]=[CH:7]2>C(O)(=O)C>[Br:1][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([F:3])[CH:5]=2)[C:10](=[O:14])[N:9]([CH3:15])[CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 693999762-N-methyl-6-fluoro-1-isoquinolinone

Product 1

HCID 1180215214-Bromo-6-fluoro-2-methylisoquinolin-1-oneYield 84.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (232 mg, 1.45 mmol, 0.097 mL) in acetic acid (1.0 mL) was added dropwise, quickly to 6-fluoro-2-methylisoquinolin-1-one (283 mg, 1.61 mmol) in acetic acid (7.0 mL) under N2 and cooled in an ice bath. The ice bath was removed and the thick suspension was stirred for 10 min at room temperature. Ice and water and ethyl acetate were added. Extractive work up with ethyl acetate, washing with aqueous 0.5 N NaOH, H2O, saturated aqueous KHSO4 and brine, gave the title compound as a cream solid (313 mg) which was carried on without purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice bath was removed
  3. additionIce and water and ethyl acetate were added
  4. washwashing with aqueous 0.5 N NaOH, H2O, saturated aqueous KHSO4 and brine

Sources & evidence

ORD record
ord-cfad2792f67d4a949890e4dcedf169f7
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

Loading…