Water → HCID 88742077, compound

HRID 905245Notes

Reaction equation

HRID 905245 reaction equation
[K].[CH3:2][C:3]1([CH3:14])[CH:5]([CH:6]=[C:7]2[CH2:10][CH2:9][CH2:8]2)[CH:4]1[C:11]([OH:13])=[O:12].[F:15][C:16]1[C:21]([CH2:22]Br)=[C:20]([F:24])[C:19]([F:25])=[C:18]([F:26])[C:17]=1[F:27].O>CN(C)C=O>[CH3:2][C:3]1([CH3:14])[CH:5]([CH:6]=[C:7]2[CH2:10][CH2:9][CH2:8]2)[CH:4]1[C:11]([O:13][CH2:22][C:21]1[C:20]([F:24])=[C:19]([F:25])[C:18]([F:26])=[C:17]([F:27])[C:16]=1[F:15])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 74484Pentafluorobenzyl bromideHCID 5462222PotassiumHCID 13241312HCID 13241312, compound

Product 1

HCID 88742077HCID 88742077, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.6 g (0.0165 mol) of the potassium salt of 2,2-dimethyl-3-cyclobutylidenemethylcyclopropanecarboxylic acid were dissolved in 50 ml of dimethylformamide and the solution was heated to 110° C., together with 4.3 g (0.0165 mol) of pentafluorobenzyl bromide, for 3 hours. After the reaction had ended, the reaction mixture was poured into 150 ml of water and extracted twice with 100 ml of methylene chloride each time. The organic phase was then extracted by shaking twice with 100 ml of water each time and then dried over sodium sulphate. The solvent was stripped off in vacuo and last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 4.0 g (67.1% of theory) of pentafluorobenzyl 2,2-dimethyl-3-cyclobutylidenemethylcyclopropanecaboxylate were obtained as a brown oil with the refractive index nD30 :1.4850.

Workup

  1. extractionextracted twice with 100 ml of methylene chloride each time
  2. extractionThe organic phase was then extracted
  3. dry with materialdried over sodium sulphate
  4. customwere removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-6de6e7afc55540afb8d94d4974746cae
Source dataset
uspto-grants-1983_12
Patent number
US04423066

Reaction notes

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