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

HRID 2307775Notes

Reaction equation

HRID 2307775 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].CO>C1COCC1>[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

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 33B (1.1 g, 3.57 mmol) in THF (20 mL) at room temperature was treated with 1N NH3 in methanol (7.14 mL, 7.14 mmol), stirred for 24 hours, and filtered. The filter cake was washed with diethyl ether (100 mL) to provide the desired product (0.4 g, 52%).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with diethyl ether (100 mL)

Sources & evidence

ORD record
ord-6eff39abd44446cbb926b44b31759558
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

Loading…