Hydrogen Bromide → 5-Bromoisoindoline

HRID 1494839Notes

Reaction equation

HRID 1494839 reaction equation
C1(C)C=CC(S([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Br:19])[CH:16]=3)[CH2:11]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.Br>C(O)(=O)CC>[Br:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH2:11][NH:10][CH2:18]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 151678985-Bromo-2-(p-tolylsulfonyl)isoindoline

Product 1

HCID 147958715-BromoisoindolineYield 34.7%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

The procedure of Reference Example 6-(3) was followed using 12.8 g of 2-(p-toluenesulfonyl)-5-bromoisoindoline, 12 g of phenol, 160 ml of 48% hydrobromic acid, and 30 ml of propionic acid. Purification of the crude product by vacuum distillation gave 2.5 g of 5-bromoisoindoline.

Workup

  1. customPurification of the crude product
  2. distillationby vacuum distillation

Sources & evidence

ORD record
ord-6939f8db48284c3c8f0e9c9887411778
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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