Water → Dibenzo[a,e]cyclopropa[c]cyclohepten-6(1H)-one, 1,1-difluoro-1a,10b-dihydro-

HRID 1168559Notes

Reaction equation

HRID 1168559 reaction equation
Cl[C:2]([F:7])([F:6])[C:3]([O-])=O.[Na+].[CH:9]1[C:19]2[CH:18]=C[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1.O>COCCOCCOC>[F:6][C:2]1([F:7])[CH:18]2[CH:3]1[C:23]1[CH:22]=[CH:21][CH:20]=[CH:16][C:15]=1[C:14](=[O:24])[C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:19]=12

Participants

5

Reactant 3

HCID 962WaterHCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 12073911Dibenzo[a,e]cyclopropa[c]cyclohepten-6(1H)-one, 1,1-difluoro-1a,10b-dihydro-Yield 45.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

A solution of sodium chlorodifluoroacetate (350 g) in diglyme (1400 mL) was added dropwise over 4 to 8 hours, preferably over 6 hours, to a solution of 5H-dibenzo[a,d]cyclo-hepten-5-one (25 g) in diglyme (500 mL), with stirring, and under nitrogen, maintaining the reaction temperature at 160°-165° C. The cooled reaction mixture was poured into water (1.8 L) and extracted with ether (1.8 L). The organic phase was washed with water, dried over sodium sulfate (Na2SO4), and evaporated. The residue was recrystallized from ethanol, then from acetone/hexane to give 14 g of 1,1-difluoro-1a,10b-dihydrodibenzo[a,e]cyclopropa[c]-cyclohepten-6(1H)-one.

Workup

  1. temperatureunder nitrogen, maintaining the reaction temperature at 160°-165° C
  2. customThe cooled reaction mixture
  3. extractionextracted with ether (1.8 L)
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate (Na2SO4)
  6. customevaporated
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5d442f58fa0341a39669305365eae07f
Source dataset
uspto-grants-2003_09
Patent number
US06624304B1

Reaction notes

Loading…