Potassium Hydroxide → 2-Chloro-1,1-difluoro-3-(p-methoxyphenyl)-2-cyclobutene

HRID 1578801Notes

Reaction equation

HRID 1578801 reaction equation
[OH-].[K+].[Cl:3][C:4]1(Cl)[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH2:6][C:5]1([F:17])[F:16]>C(O)C>[Cl:3][C:4]1[C:5]([F:16])([F:17])[CH2:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21425195Benzene, 1-(2,2-dichloro-3,3-difluorocyclobutyl)-4-methoxy-

Product 1

HCID 214251982-Chloro-1,1-difluoro-3-(p-methoxyphenyl)-2-cyclobuteneYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.2 g. (0.049 mole) of 85% potassium hydroxide in 60 ml. of absolute ethanol there is added 10.7 g. (0.04 mole) of 2,2-dichloro-1,1-difluoro-3-(p-methoxyphenyl)cyclobutane. The mixture is heated at reflux for 1 hr. and then cooled to room temperature. Precipitated potassium chloride is removed by filtration and the filtrate concentrated to about 20 ml. About 70 ml. of water is added and the mixture is extracted with three 50 ml. portions of ether. The extract is washed (water 70 ml.), dried and the solvent distilled. The residual material constitutes a 96% yield of desired intermediate suitable for use in the next step. A small sample was distilled for analysis, b.p. 67°C. (0.02 mm) ND27 1.5597.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1 hr
  3. customPrecipitated potassium chloride is removed by filtration
  4. concentrationthe filtrate concentrated to about 20 ml
  5. additionof water is added
  6. extractionthe mixture is extracted with three 50 ml
  7. washThe extract is washed (water 70 ml.)
  8. customdried
  9. distillationthe solvent distilled

Sources & evidence

ORD record
ord-e3617858362449d9b67a02a06cbc29df
Source dataset
uspto-grants-1976_02
Patent number
US03939196

Reaction notes

Loading…