Hydrogen Bromide → 5-Chloroisoindoline hydrochloride

HRID 2355694Notes

Reaction equation

HRID 2355694 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>[ClH:19].[ClH:19].[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

7

Reactant 4

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

Product 2

HCID 313Hydrochloric AcidHCID 498535025-Chloroisoindoline hydrochlorideYield 145.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 2-(p-toluensulfonyl)-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 twice with 50 ml of ethyl acetate. The water layer was basified with aqueous sodium hydroxide solution and extracted with ethyl acetate three times. The extract was concentrated and the crude was diluted with 4N HCl/Dioxane and stirred for 15 minutes. Evaporate HCl, azeotrope with toluene three times to obtained 0.3 g of 5-Chloro-2,3-dihydro-1H-isoindole hydrochloride as a black solid. MS: [M+H]+ 153-15

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customThe resultant reaction mixture
  3. extractionextracted twice with 50 ml of ethyl acetate
  4. extractionextracted with ethyl acetate three times
  5. concentrationThe extract was concentrated
  6. additionthe crude was diluted with 4N HCl/Dioxane

Sources & evidence

ORD record
ord-aa24a40d7173496096d7fba3c5eebab8
Source dataset
uspto-grants-2010_07
Patent number
US07754725B2

Reaction notes

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