Phenol → 2-(4-Phenoxybutyl)-1H-isoindole-1,3(2H)-dione

HRID 2239552Notes

Reaction equation

HRID 2239552 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CC#N>[O:23]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2[C:8](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]1=[O:16])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 996Phenol2×HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 166375972-(4-Phenoxybutyl)-1H-isoindole-1,3(2H)-dioneYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(4-bromobutyl)phthalimide) (2.00 g, 7.09 mmol), phenol (0.67 g, 7.09) and K2CO3 (1.96 g, 14.18 mmoml) in dry MeCN (30 ml) was stirred at rt for 66 h. The reaction mixture was then warmed to 50° C. for 20 h before more phenol (0.33 mg, 3.54 mmol) was added and the resulting mixture was warmed at reflux. After 4 h EtOAc was added, the mixture was washed with brine, then 1N NaOH, and brine again before evaporated the organic phase to dryness to give the title compound (1.11 g, 53%) which was used without further purification. 1H NMR (500 MHz CDCl3): δ 7-90-7.83 (m, 2H), 7.76-7.70 (m, 2H), 7.28 (t, 2H), 6.93 (t, 1H), 6.89 (d, 2H), 4.01 (t, 2H), 3.79 (t, 2H), 1.96-1.82 (m, 4H); Mass Spectrum: M+H+ 296.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was warmed
  3. temperatureat reflux
  4. washthe mixture was washed with brine
  5. custom1N NaOH, and brine again before evaporated the organic phase to dryness

Sources & evidence

ORD record
ord-72975074d9344bfb9ba46380cebebd3e
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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