N-bromobutanimide → 3-Bromo-4,5,6-trimethoxyphthalide

HRID 259098Notes

Reaction equation

HRID 259098 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[C:9]2[C:4]=1[CH2:5][O:6][C:7]2=[O:8].[Br:17]N1C(=O)CCC1=O.N(CCCC#N)=NCCCC#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH:5]1[C:4]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[C:12]([O:13][CH3:14])[C:3]=2[O:2][CH3:1])[C:7](=[O:8])[O:6]1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 2308694,5,6-trimethoxy-2-benzofuran-1(3H)-oneHCID 14151322Azobisbutyronitrile

Product 1

HCID 214230393-Bromo-4,5,6-trimethoxyphthalide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4,5,6-Trimethoxyphthalide (11.4 gms; 0.05 mole), N-bromosuccinimide (8.9 gms; 0.05 mole) and azobisbutyronitrile (0.1 gms) were refluxed gently in dry carbon tetrachloride (200 mls) for 2 hours. The solution was cooled, the succinimide filtered off and the solvent removed in vacuo, leaving a yellowish solid which fumed in the air.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe succinimide filtered off
  3. customthe solvent removed in vacuo
  4. customleaving a yellowish solid which

Sources & evidence

ORD record
ord-135b9d78d4b64f47ac018ecbeec80aeb
Source dataset
uspto-grants-1977_07
Patent number
US04036829

Reaction notes

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