Ammonia → 6-Bromo-2,3-dihydro-1H-isoindol-1-one

HRID 1471836Notes

Reaction equation

HRID 1471836 reaction equation
[NH3:1].C[O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[CH2:12]Br>CO>[Br:11][C:9]1[CH:10]=[C:5]2[C:6]([CH2:12][NH:1][C:4]2=[O:3])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate

Product 1

HCID 222209196-Bromo-2,3-dihydro-1H-isoindol-1-oneYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a saturated solution of NH3 in CH3OH (50 mL) was added 5-bromo-2-bromomethyl-benzoic acid methyl ester (4.8 g, 16 mmol). The reaction mixture was stirred in a sealed tube at 40° C. overnight. The mixture was cooled to room temperature and the resultant white solid was collected to afford 6-bromoisoindolin-1-one (2.2 g, 67%). 1H NMR (400 MHz, DMSO) δ 8.71 (s, 1H), 7.75 (d, 2H), 7.53 (s, 1H), 4.32 (s, 2H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe resultant white solid was collected

Sources & evidence

ORD record
ord-e35a98288afd456584c32733c8f9e8e4
Source dataset
uspto-grants-2015_04
Patent number
US09012473B2

Reaction notes

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