Potassium tert-butoxide → 1,2-Dichloro-3-(trifluoroprop-1-YN-1-YL)benzene

HRID 1607910Notes

Reaction equation

HRID 1607910 reaction equation
Cl[C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[Cl:11].CC([O-])(C)C.[K+]>C(O)(C)(C)C>[Cl:11][C:5]1[C:6]([Cl:10])=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]#[C:2][C:12]([F:15])([F:13])[F:14]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 54504845(2-Chloro-3,3,3-trifluoropropen-1-yl)-2,3-dichlorobenzene

Product 1

HCID 198498191,2-Dichloro-3-(trifluoroprop-1-YN-1-YL)benzene

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of 31.7 g of (2-chloro-3,3,3-trifluoropropen-1-yl)-2,3-dichlorobenzene in 50 ml of tert-butanol, there is added dropwise at RT a solution of 14.1 g of potassium tert-butylate in 750 ml of tert-butanol in such a manner that the temperature of the reaction solution does not exceed 30° C. After continued stirring at RT for 18 h, the mixture is taken up in ice-water and extracted with ether. The organic phases are combined, washed with water and sodium chloride solution, and concentrated by evaporation. There is thus obtained, after distillation in vacuo, 2,3-dichloro-(3,3,3-trifluoropropyn-1-yl)-benzene in the form of colourless oil, b.p. 92°-98° C. at 22 mb (compound No. 2.27).

Workup

  1. customdoes not exceed 30° C
  2. extractionextracted with ether
  3. washwashed with water and sodium chloride solution
  4. concentrationconcentrated by evaporation
  5. customThere is thus obtained
  6. distillationafter distillation in vacuo, 2,3-dichloro-(3,3,3-trifluoropropyn-1-yl)-benzene in the form of colourless oil, b.p. 92°-98° C. at 22 mb (compound No

Sources & evidence

ORD record
ord-c9c5eabdcb264a7281d296babd8fe870
Source dataset
uspto-grants-1989_09
Patent number
US04868202

Reaction notes

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