Ammonia → 4-Bromoisoindolin-1-one

HRID 1059263Notes

Reaction equation

HRID 1059263 reaction equation
[Br:1][C:2]1[C:3]([CH2:12]Br)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].[NH3:14]>CO.C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]2[C:3]=1[CH2:12][NH:14][C:5]2=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoate

Product 1

HCID 219075094-Bromoisoindolin-1-oneYield 76%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 3-bromo-2-(bromomethyl)benzoate (1.28 g) was dissolved in a 11% solution of ammonia in methanol-THF mixed solution (3:2, 25 ml) and the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and the residue was washed with saturated brine. Recrystallization from ethyl acetate-hexane gave the title compound (671 mg, 76%) as colorless needle crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with saturated brine
  3. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6c3f4318b73d4bcfa5a8561fbb63e195
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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