Phenol → 4-fluoro-2,3-dihydro-1H-isoindole

HRID 1494835Notes

Reaction equation

HRID 1494835 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[F:19])[CH2:11]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.C(O)(=O)CC>Br>[F: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 996PhenolHCID 1032Propionic AcidHCID 15167892HCID 15167892, compound

Product 1

HCID 147958674-fluoro-2,3-dihydro-1H-isoindoleYield 55.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The procedure described in Reference Example 6-(3) was followed using 2.30 g of 2-(p-toluenesulfonyl)-4-fluoroisoindoline, 2.30 g of phenol, 20 ml of 48% hydrobromic acid, and 3.5 ml of propionic acid. Purification of the crude product by vacuum distillation (bath temperature: 110°-150° C., pressure: 7 mmHg) gave 604 mg of 4-fluoroisoindoline.

Workup

  1. customPurification of the crude product
  2. distillationby vacuum distillation (bath temperature: 110°-150° C., pressure: 7 mmHg)

Sources & evidence

ORD record
ord-f63a0bf8385249e9b7243b9591cd92ac
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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