Hydrogen Bromide → 5-Chloroisoindoline

HRID 1494834Notes

Reaction equation

HRID 1494834 reaction equation
C1(C)C=CC(S([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:19])[CH:16]=3)[CH2:11]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.Br.C(O)(=O)CC>O>[Cl:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH2:11][NH:10][CH2:18]2

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 996PhenolHCID 1032Propionic AcidHCID 151678915-Chloro-2-tosylisoindoline

Product 1

HCID 147958665-ChloroisoindolineYield 51.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 2-(p-toluenesulfonyl)-5-chloroisoindoline and 1.0 g of phenol were added to a mixture of 8 ml of 48% hydrobromic acid and 1.4 ml of propionic acid, and the mixture was refluxed for 6 hours. The resultant reaction mixture was diluted with 10 ml of water and extracted 2 times with 50 ml of ether. The water layer was basified with aqueous sodium hydroxide solution and extracted with 50 ml of ether 4 times. The extract was concentrated and the residue was purified by vacuum distillation (bath temperature: 130°-140 ° C., pressure: 7 mmHg) to obtain 256 mg of 5-chloroisoindoline.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customThe resultant reaction mixture
  3. extractionextracted 2 times with 50 ml of ether
  4. extractionextracted with 50 ml of ether 4 times
  5. concentrationThe extract was concentrated
  6. distillationthe residue was purified by vacuum distillation (bath temperature: 130°-140 ° C., pressure: 7 mmHg)

Sources & evidence

ORD record
ord-86f1462dbf59402f97b4d9191888c90b
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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