Dimethylformamide → 2-[2-(4-Fluorophenyl)-2-oxoethyl]cycloheptan-1-one

HRID 1973470Notes

Reaction equation

HRID 1973470 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.CN(C)[CH:14]=[O:15].N1([C:22]2[CH2:28][CH2:27]C[CH2:25][CH2:24][CH:23]=2)CCCC1>O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7][CH:25]2[CH2:24][CH2:23][CH2:22][CH2:28][CH2:27][C:14]2=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 5860371-(1-Pyrrolidinyl)-1-cycloheptene

Product 1

HCID 214915712-[2-(4-Fluorophenyl)-2-oxoethyl]cycloheptan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 32,6 g (0.15 mole) of p-fluorophenacylbromide in 100 ml. of dry dimethylformamide is added dropwise to a cooled solution of 25 g (0.15 mole) of 1-pyrrolidino-1-cycloheptene in 100 ml. of dry dimethylformamide. After stirring at ambient temperature for 20 hours, and at 100° C. for 5 hours, 250 ml. of water are added, and the mixture is stirred for 3 hours. The reaction mixture is poured into 1500 ml. of water, extracted with chloroform, and the chloroform extract is washed with water and dried. Removal of the chloroform leaves 2-(p-fluorophenacyl)cycloheptanone as an oil. Infrared and nuclear magnetic resonance spectra confirm the above structure.

Workup

  1. waitat 100° C. for 5 hours
  2. stirringthe mixture is stirred for 3 hours
  3. additionThe reaction mixture is poured into 1500 ml
  4. extractionof water, extracted with chloroform
  5. extractionthe chloroform extract
  6. washis washed with water
  7. customdried
  8. customRemoval of the chloroform

Sources & evidence

ORD record
ord-130dc5e3a4ec4299b7ce9e9d0ce5ab4d
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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