Tetrahydrofuran → 4-Bromoisoindolin-1-one

HRID 1712950Notes

Reaction equation

HRID 1712950 reaction equation
[Br:1][C:2]1[C:3]([CH2:12]Br)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].C1COCC1.[OH-].[NH4+:20]>O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]2[C:3]=1[CH2:12][NH:20][C:5]2=[O:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoate

Product 1

HCID 219075094-Bromoisoindolin-1-oneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 3-bromo-2-(bromomethyl)benzoate (27 mmol) in THF (100 mmol) was added ammonium hydroxide (9 mL) dropwise at rt. The reaction mixture was allowed to stir overnight and then diluted with 30 mL of water. The solution was extracted with DCM, dried over Na2SO4, filtered and concentrated to give 4-bromoisoindolin-1-one (5.20 g, 91%).

Workup

  1. extractionThe solution was extracted with DCM
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b1650367a16449beb60bcaef47cf07d9
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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