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

HRID 2420909Notes

Reaction equation

HRID 2420909 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH2:11]Br.[NH3:14]>CO>[Br:10][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:3](=[O:2])[NH:14][CH2:11]2

Participants

4

Reactant 2

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

Product 1

HCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

4-Bromo-2-bromomethylbenzoic acid methyl ester (0.70 g, 2.3 mmol) and sat. NH3 in MeOH (3 mL) were placed in a sealed tube. The mixture was heated at 40° C. overnight. After cooling to rt, the solids were collected to afford 5-bromoisoindolin-1-one (0.43 g, 89%). 1H NMR (DMSO-d6, 400 MHz) δ 8.62 (br s, 1H), 7.81 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.58 (d, J=7.6 Hz, 1H), 4.35 (s, 2H).

Workup

  1. temperatureAfter cooling to rt
  2. customthe solids were collected

Sources & evidence

ORD record
ord-eafc7c49d83b42c09209f0a43bc0c44a
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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