Hydrogen Bromide → 5-Bromoisoindoline

HRID 1478851Notes

Reaction equation

HRID 1478851 reaction equation
Br.C(O)(=O)CC.C1(O)C=CC=CC=1.[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][N:19](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:18]2>O>[Br:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][NH:19][CH2:18]2

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 996PhenolHCID 1032Propionic AcidHCID 151678985-Bromo-2-(p-tolylsulfonyl)isoindoline

Product 1

HCID 147958715-Bromoisoindoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of aqueous hydrobromic acid (16 mL, 48% solution in water), propionic acid (2.8 mL) and phenol (2 g) was added 5-bromo-2-(p-tolylsulfonyl)isoindoline (2.4 g, 6.8 mmol). The resulting mixture was heated to reflux and stirred at this temperature for 10 hr then cooled to room temperature. This mixture was diluted with water (20 mL) and extracted with ether (2×50 mL). The aqueous extract was brought to pH 14 with 5M sodium hydroxide solution. This solution was extracted with ether (3×). The ether extract is washed with brine, dried over magnesium sulfate, and concentrated to give the title compound as an oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. extractionextracted with ether (2×50 mL)
  4. extractionThe aqueous extract
  5. extractionThis solution was extracted with ether (3×)
  6. extractionThe ether extract
  7. washis washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-10fb5cad9e054744a563ae7941fb9a86
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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