N-bromobutanimide → 3-Bromo-5,6-dimethoxy-phthalide

HRID 1578760Notes

Reaction equation

HRID 1578760 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:8](=[O:9])[O:7][CH2:6]2.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8](=[O:9])[O:7]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2304605,6-Dimethoxy-3H-isobenzofuran-1-one

Product 1

HCID 111965723-Bromo-5,6-dimethoxy-phthalide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5,6-Dimethoxyphthalide (5.82 g; 0.03 mole.), N-bromosuccinimide (5.34 g; 0.03 mole.) and α-azo-isobutyronitrile (0.1 g.) were gently refluxed in dry carbon tetrachloride (150 ml.) for 2 hours.

Sources & evidence

ORD record
ord-54c1e9b7e0fc4df38e6596eb7b5a13b5
Source dataset
uspto-grants-1976_02
Patent number
US03939180

Reaction notes

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