Hydrogen Bromide → 5-Bromoisoindoline

HRID 576622Notes

Reaction equation

HRID 576622 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-2f17bd5bbf5c4d2f836c84c8c8711e01
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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