Hydrogen Bromide → 4-bromo-2,3-dihydro-1H-isoindole

HRID 1494838Notes

Reaction equation

HRID 1494838 reaction equation
C1(C)C=CC(S([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[Br:19])[CH2:11]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.Br>C(O)(=O)CC>[Br:19][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH2:18][NH:10][CH2:11]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 151678974-Bromo-2-tosylisoindoline

Product 1

HCID 147958704-bromo-2,3-dihydro-1H-isoindoleYield 92.5%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

The procedure of Reference Example 6-(3) was followed using 9.61 g of 2-(p-toluenesulfonyl)-4-bromoisoindoline, 10 g of phenol, 120 ml of 48% hydrobromic acid, and 20 ml of propionic acid. Purification of the crude product by vacuum distillation gave 5.0 g of 4-bromoisoindoline.

Workup

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

Sources & evidence

ORD record
ord-823fc84af3f249209d928ad8ba93a319
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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