N-bromobutanimide → Bromo-6-Chloro-Phthalide

HRID 259097

Reaction equation

HRID 259097 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][O:7][C:8]2=[O:9])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(CCCC#N)=NCCCC#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:8](=[O:9])[O:7]1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 71741656-Chloro-3H-isobenzofuran-1-oneHCID 14151322Azobisbutyronitrile

Product 1

HCID 12298538Bromo-6-Chloro-Phthalide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

6-Chlorophthalide (7.66 gms; 0.0452 mole), N-bromosuccinimide (8.1 gms; 0.0452 mole) and azobisbutyronitrile (0.1 gm) were gently refluxed in dry carbon tetrachloride (150 ml.) for 11/2 hours. On cooling, the succinimide was filtered off and the solvent removed in vacuo to leave a yellow solid, which was used immediately. Yield 9.57 gms. 86.2%

Workup

  1. temperatureOn cooling
  2. filtrationthe succinimide was filtered off
  3. customthe solvent removed in vacuo
  4. customto leave a yellow solid, which

Sources & evidence

ORD record
ord-f756589f3d0541b297d5073c29ad0be3
Source dataset
uspto-grants-1977_07
Patent number
US04036829

Linked notes

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