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

HRID 2427500Notes

Reaction equation

HRID 2427500 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH2:11]Br.[OH-].[NH4+:15]>N.CO>[Br:10][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:3](=[O:2])[NH:15][CH2:11]2

Participants

5

Reactant 2

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

Product 1

HCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneYield 90%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

4-Bromo-2-bromomethyl-benzoic acid methyl ester (3.70 g) was suspended in 2M NH3 in MeOH (36 mL) and concentrated ammonium hydroxide (12 mL) for eighteen hours. The solid product was filtered to provide the title compound as a colourless solid (2.30 g, 90%). 1H NMR (300M, CDCl3): δ 7.68 (m, 3H), 4.44 (s, 2H).

Workup

  1. filtrationThe solid product was filtered

Sources & evidence

ORD record
ord-08af4fdb718842e0b5846b20d14aa1ea
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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