Hydrogen Bromide → 2,3-dihydro-1H-isoindole-5,6-diol hydrobromide

HRID 704455Notes

Reaction equation

HRID 704455 reaction equation
[BrH:1].C1(O)C=CC=CC=1.C[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[O:20]C)[CH2:16][N:15](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:14]2>C(O)(=O)CC>[BrH:1].[OH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[OH:20])[CH2:16][NH:15][CH2:14]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 100881951H-Isoindole, 2,3-dihydro-5,6-dimethoxy-2-[(4-methylphenyl)sulfonyl]-

Product 1

HCID 200743492,3-dihydro-1H-isoindole-5,6-diol hydrobromideYield 61.4%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

360 ml of 47% hydrobromic acid, 45 m1 of phenol and 60 ml of propionic acid were added to 60 g (0.18 mol) of 5,6-dimethoxy-2-p-tolylsulfonylisoindoline, and the mixture was refluxed for 4 hours under vigorous stirring under a nitrogen atmosphere. The reaction solution was evaporated under reduced pressure to dryness, and 120 ml of 47% hydrobromic acid was added to the residue. The mixture was again refluxed under a nitrogen atmosphere for 3 hours. The reaction solution was cooled, and then 300 ml of water and 300 ml of chloroform were added thereto. The water layer was separated, and subjected to active carbon treatment. The water layer was evaporated under reduced pressure to dryness, and the crystalline residue was washed with ether/ethanol (1/1) to obtain 25.62 g (yield: 61.4%) of the above identified compound.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe reaction solution was evaporated under reduced pressure to dryness, and 120 ml of 47% hydrobromic acid
  3. additionwas added to the residue
  4. temperatureThe mixture was again refluxed under a nitrogen atmosphere for 3 hours
  5. temperatureThe reaction solution was cooled
  6. addition300 ml of water and 300 ml of chloroform were added
  7. customThe water layer was separated
  8. customThe water layer was evaporated under reduced pressure to dryness
  9. washthe crystalline residue was washed with ether/ethanol (1/1)
  10. customto obtain 25.62 g (yield: 61.4%) of the

Sources & evidence

ORD record
ord-e9980326d3a2480192dd21aec0e219a6
Source dataset
uspto-grants-1991_01
Patent number
US04987235

Reaction notes

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