Phenol → 5-Fluoro-2,3-dihydro-1H-isoindole

HRID 1494837Notes

Reaction equation

HRID 1494837 reaction equation
C1(C)C=CC(S([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:19])[CH:16]=3)[CH2:11]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.C(O)(=O)CC>Br>[F: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 996PhenolHCID 1032Propionic AcidHCID 151678952-(p-Toluenesulfonyl)-5-fluoroisoindoline

Product 1

HCID 147958695-Fluoro-2,3-dihydro-1H-isoindoleYield 0.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The procedure of Reference Example 6-(3) was followed using 10.2 g of 2-(p-toluenesulfonyl)-5-fluoroisoindoline, 10 g of phenol, 150 ml of 48% hydrobromic acid, and 25 ml of propionic acid. Purification of the crude product by vacuum distillation gave 5.0 mg of 5-fluoroisoindoline.

Workup

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

Sources & evidence

ORD record
ord-2fbf56063a0940459b2e1d536676d31f
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

Loading…