4-Chlorobenzaldehyde → 2-(4-Chlorophenyl)cyclobutanone

HRID 1482437Notes

Reaction equation

HRID 1482437 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH:15]1([S+](C2C=CC=CC=2)C2C=CC=CC=2)[CH2:17][CH2:16]1.CC(C)([O-:34])C.[K+].F[B-](F)(F)F.[H+]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[CH2:17][CH2:15][C:16]2=[O:34])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 28118Tetrafluoroboric acidHCID 2724210Cyclopropyldiphenylsulphonium tetrafluoroborateHCID 23665647Potassium tert-butoxide

Product 1

HCID 898230052-(4-Chlorophenyl)cyclobutanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-chloro-benzaldehyde (142 mg, 1 mmol) and cyclopropyldiphenylsulfonium tetrafluoroborate (317 mg, 1 mmol) in 10 ml dry THF, cooled to 0° C., was added dropwise, with stirring, a slurry of potassium tert. butoxide (1.4 ml 1M). After addition was complete the reaction was stirred 30 min. and 1M tetrafluoroboric acid (10% in THF) (10 ml) was added. The mixture was allowed to warm to room temperature and was taken up into ether and the ether solution was washed with saturated NaHCO3, brine and water and was dried. Filtration and concentration by rotary evaporation gave an oil. Chromatography over silica gel and elution i-Hx:ether 5:1 gave 2-(4-chlorophenyl)cyclobutanone as an oil. (180 mg, 83%).

Workup

  1. additionwas added dropwise
  2. additionAfter addition
  3. stirringwas stirred 30 min.
  4. washthe ether solution was washed with saturated NaHCO3, brine and water
  5. customwas dried
  6. filtrationFiltration and concentration
  7. customby rotary evaporation
  8. customgave an oil
  9. washChromatography over silica gel and elution i-Hx

Sources & evidence

ORD record
ord-1cdd278f15cd4adb80718235a3b87771
Source dataset
uspto-grants-2016_08
Patent number
US09414589B2

Reaction notes

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