Potassium Carbonate → HCID 59848141, compound

HRID 1803802Notes

Reaction equation

HRID 1803802 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>O.CC(C)=O>[C:16]1(=[O:25])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:9][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([Br:8])[CH:5]=2)[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]12

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 122803,5-DibromophenolHCID 2855718-Crown-6HCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 59848141HCID 59848141, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3,5-dibromophenol (970 mg, 3.85 mmol) was recrystallized from hexanes. After removal of solvent, N-(4-bromobutyl)phthalimide (1.38 g, 4.89 mmol), K2CO3 (1.88 g, 13.6 mmol), 18-crown-6 (53 mg, 0.20 mmol), and acetone (20 mL) were added. This was refluxed for 1 hour, and then poured into 100 mL of water. The aqueous layer was extracted with dichloromethane (4×30 mL). The organic layers were combined, washed with water, saturated NaHCO3, and brine, then dried over MgSO4 and filtered. Removal of solvent yielded a white solid, which was purified by column chromatography (4:1 hexanes:CH2Cl2) followed by recrystallization in hexanes to yield colorless needles (650 mg, 87%). 1H NMR (CDCl3): 7.860 (m, 2H); 7.733 (m, 2H); 7.220 (t, J=1.6 Hz, 1H); 6.964 (d, J=2.0 Hz, 2H); 3.962 (t, J=6.0 Hz, 2H); 3.770 (t, J=6.6 Hz, 2H); 1.846 (m, 4H).

Workup

  1. additionwere added
  2. temperatureThis was refluxed for 1 hour
  3. extractionThe aqueous layer was extracted with dichloromethane (4×30 mL)
  4. washwashed with water, saturated NaHCO3, and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customRemoval of solvent
  8. customyielded a white solid, which
  9. customwas purified by column chromatography (4:1 hexanes:CH2Cl2)
  10. customfollowed by recrystallization in hexanes

Sources & evidence

ORD record
ord-9ea018bb47c34123b6daad7641bd5012
Source dataset
uspto-grants-2013_01
Patent number
US08354239B2

Reaction notes

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