HCID 20343345, compound → HCID 54134967, compound

HRID 2050049Notes

Reaction equation

HRID 2050049 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]1[C:9]([O-:11])=[O:10].[Na+].[F:14][C:15]1[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=1)[O:18][C:19]1[CH:20]=[C:21]([C:24]([F:27])=[CH:25][CH:26]=1)[CH2:22]Br>CN(C)C=O>[CH3:1][C:2]1([CH3:12])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]1[C:9]([O:11][CH2:22][C:21]1[C:24]([F:27])=[CH:25][CH:26]=[C:19]([O:18][C:17]2[CH:28]=[CH:29][CH:30]=[C:15]([F:14])[CH:16]=2)[CH:20]=1)=[O:10]

Participants

4

Reactant 2

HCID 20343345HCID 20343345, compoundHCID 23663704Sodium 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Product 1

HCID 54134967HCID 54134967, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.9 g (0.03 mol) of sodium 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate were dissolved in 150 ml of dimethylformamide and heated, with 8.0 g (0.027 mol) of 3-(3-fluorophenoxy)-6-fluorobenzyl bromide, for 4 hours at 120° C. After completion of the reaction, the dimethylformamide was distilled off in vacuo and the residue was taken up in 200 ml of methylene chloride. This solution was then extracted by shaking twice with 150 ml of water, the organic phase was dried over sodium sulphate and the solvent was stripped off in vacuo. The last remnants of solvent were removed by brief incipient distillation at 70° C. (bath temperature)/1 mm Hg. 8.0 g (71% of theory) of 3-(3-fluorophenoxy)-6-fluorobenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate were obtained as a yellow oil having a refractive index nD24 of 1.5395.

Workup

  1. customAfter completion of the reaction
  2. distillationthe dimethylformamide was distilled off in vacuo
  3. extractionThis solution was then extracted
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. customThe last remnants of solvent were removed by brief incipient distillation at 70° C. (bath temperature)/1 mm Hg

Sources & evidence

ORD record
ord-60f8dc4c5ea74772bd87a4a73093de04
Source dataset
uspto-grants-1980_04
Patent number
US04199596

Reaction notes

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