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

HRID 2203216Notes

Reaction equation

HRID 2203216 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.[NH3:14].[OH-].[NH4+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:7])[NH:14][CH2:12]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneYield 61%

Procedure

Methyl 4-bromo-2-(bromomethyl)benzoate (0.157 g, 0.510 mmol) was suspended in ammonia (2M solution in MeOH, 0.255 mL, 1.784 mmol). Ammonium hydroxide (0.517 mL, 7.65 mmol) was added and the mixture was stirred at RT overnight. A resulting white solid was collected by vacuum filtration, washed with water, and dried under high vacuum overnight to give the title compound as a white solid (0.066 g, 61%). 1H NMR (500 MHz, CDCl3) δ ppm 4.45 (s, 2 H), 6.35 (br s, 1 H), 7.60-7.68 (m, 2 H), 7.74 (d, J=8.30 Hz, 1 H); ESI-MS m/z [M+H]+ 212.3.

Workup

  1. filtrationA resulting white solid was collected by vacuum filtration
  2. washwashed with water
  3. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-c903d8fe25e543daa2451c805b4e0c06
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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