Phenol → 5-Bromoisoindoline hydrobromide

HRID 1584821Notes

Reaction equation

HRID 1584821 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.C(O)(=O)CC>Br>[BrH:19].[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 996PhenolHCID 1032Propionic AcidHCID 151678985-Bromo-2-(p-tolylsulfonyl)isoindoline

Product 1

HCID 193583595-Bromoisoindoline hydrobromideYield 176.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

In 25 ml of 47% hydrobromic acid was suspended 5.0 g of 2-(p-toluenesulfonyl)-5-bromoisoindoline, and 4.0 g of phenol and 15 ml of propionic acid were added to the suspension, after which the resulting mixture was heated under reflux for four hours. The reaction mixture was concentrated under reduced pressure, and ethanol was added to the residue obtained, after which the resulting crystals were collected by filtration, to obtain 3.5 g of 5-bromoisoindoline hydrobromide. The hydrobromide obtained was suspended in 50 ml of methylene chloride, and 2.8 g of triethylamine was added to the suspension, after which 2.4 g of carbobenzoxy chloride was dropwise added thereto with ice-cooling. Thereafter, the resulting mixture was stirred at room temperature for one hour. The reaction mixture was added 50 ml of water and the pH was adjusted to 1 with 6N hydrochloric acid. Thereafter, the organic layer formed was separated, washed with a saturated saline solution and then dried over anhydrous magnesium chloride. The solvent was then removed by distillation under reduced pressure. To the residue thus obtained was added n-hexane, and the resulting crystals were collected by filtration to obtain 3.8 g of colorless, crystalline 2-benzyloxycarbonyl-5-bromoisoindoline.

Workup

  1. additionwere added to the suspension
  2. temperatureafter which the resulting mixture was heated
  3. temperatureunder reflux for four hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure, and ethanol
  5. additionwas added to the residue
  6. customobtained
  7. filtrationafter which the resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-7920d335026d4b09a55f2bbf20b739fe
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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