Ammonia → 5-bromo-2,3-dihydro-1H-isoindol-1-one

HRID 2171095Notes

Reaction equation

HRID 2171095 reaction equation
[NH3:1].[Br:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[C:5]([CH2:13]Br)[CH:4]=1.[OH-].[NH4+]>CO>[Br:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:11][CH:12]=1)[C:7](=[O:8])[NH:1][CH2:13]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas was purged to a stirring solution of methyl 4-bromo-2-(bromomethyl)benzoate (200 mg, 0.649 mmol) in methanol at 0° C. for 10 min. To the resulting reaction mixture ammonium hydroxide (0.5 mL) was added and the reaction mixture was stirred at RT for 16 h. The obtained solid was separated by filtration and dried to afford 5-Bromoisoindolin-1-one as a solid (100 mg, 72%).

Workup

  1. additionwas added
  2. customThe obtained solid was separated by filtration
  3. customdried

Sources & evidence

ORD record
ord-77063757633c44c98f2947d378d4dd35
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…