4-Tert-Butylaniline → 7-Bromo-2-(4-t-butyl-phenyl)-2,3-dihydro-isoindol-1-one

HRID 2251841Notes

Reaction equation

HRID 2251841 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([CH2:10]Br)=[CH:8][CH:7]=[CH:6][C:5]=1[Br:12].[C:14]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>CC(O)C>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3](=[O:13])[N:22]([C:21]1[CH:23]=[CH:24][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=1)[CH2:10]2

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 23574705Methyl 2-bromo-6-(bromomethyl)benzoate

Product 1

HCID 690317107-Bromo-2-(4-t-butyl-phenyl)-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Bromo-6-bromomethyl-benzoic acid methyl ester (214 mg) and 4-t-butylaniline (93 mg) were put into a microwave reaction vial along with 2 mL of iPrOH. The reaction was subjected to 170° C., 5 min of microwave. The solvent was evaporated and the residue was purified by silica gel chromatography (25 g, 10-20% EtOAc/hexanes) to afford 7-bromo-2-(4-t-butyl-phenyl)-2,3-dihydro-isoindol-1-one as a white powder.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography (25 g, 10-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cae5bf353df6480cbdafaa9b9bba6f93
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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