Methyl 4-bromo-2-(bromomethyl)benzoate → 5-Bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 216975

Reaction equation

HRID 216975 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([CH2:12]Br)[CH:3]=1.[CH3:14][NH2:15].CO>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:7])[N:15]([CH3:14])[CH2:12]2

Participants

3

Reactant 2

HCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoateHCID 57454252Monomethylamine methanol

Product 1

HCID 231581695-Bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

Procedure

A solution of methyl 4-bromo-2-(bromomethyl)benzoate (410 mmol) in MeNH2/MeOH (1500 mL) was heated to reflux and stirred for 18 h. The reaction mixture was concentrated and the residue was purified by chromatography on silica eluting with petroleum ether/ethyl acetate (6:1 to 3:1) to afford the sub-titled compound (48.5 g).

Workup

  1. temperatureto reflux
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by chromatography on silica eluting with petroleum ether/ethyl acetate (6:1 to 3:1)

Sources & evidence

ORD record
ord-1ee68ce3184b4df29e51592a33f34921
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Linked notes

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