Aniline → 5-Bromo-2-phenyl-2,3-dihydro-1H-isoindol-1-one

HRID 2203241Notes

Reaction equation

HRID 2203241 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(CC)CC>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12]2

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 684940215-Bromo-2-phenyl-2,3-dihydro-1H-isoindol-1-oneYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of methyl 4-bromo-2-(bromomethyl)benzoate (0.204 g, 0.662 mmol) in MeOH (5.5 mL) were added aniline (0.063 mL, 0.696 mmol) and Et3N (0.144 mL, 1.027 mmol). The mixture was heated to reflux (85° C.) for 24 hours and subsequently cooled. A white solid that formed was collected by vacuum filtration, rinsed with MeOH, and dried under vacuum to give the title compound as a white solid (0.138 g, 72% yield). 1H NMR (500 MHz, CDCl3) δ ppm 3.89 (s, 2 H), 4.85 (s, 2 H), 7.15-7.24 (m, 1 H), 7.40-7.52 (m, 2 H), 7.62-7.96 (m, 5 H); ESI-MS m/z/[M+H]+ 288.3.

Workup

  1. temperatureThe mixture was heated
  2. temperaturesubsequently cooled
  3. customA white solid that formed
  4. filtrationwas collected by vacuum filtration
  5. washrinsed with MeOH
  6. customdried under vacuum

Sources & evidence

ORD record
ord-bd11039943fb4dca8d3579b41e5b2ae0
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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