Potassium Bicarbonate → alpha-Cyano-4-fluoro-3-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

HRID 28096Notes

Reaction equation

HRID 28096 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:9]([C:10]([OH:12])=[O:11])[C:8]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].CS(O[CH:27]([C:42]#[N:43])[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[C:30]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:29]=1)(=O)=O>C1COCC1.CN(C=O)C.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH:27]([C:42]#[N:43])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:29]=3)=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acidHCID 23338840alpha-Cyano-4-fluoro-3-phenoxybenzyl methanesulfonate

Product 1

HCID 23338864alpha-Cyano-4-fluoro-3-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent2×

Procedure

3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (0.82 g, 3.40 mmol) is stirred together with 0.34 g (3.40 mmol) potassium bicarbonate in 10 ml THF/DMF (1:1) for 15 minutes. Then 1.0 g (3.40 mmol) α-cyano-4-fluoro-3-phenoxybenzyl methanesulfonate in 5 ml THF/DMF (1:1) is added and the mixture stirred for approximately 48 hours. The reaction is diluted with ether, washed with water (3×) and sat. NaCl, dried and solvent is removed. The crude product is purified by prep. TLC developing with 10% ethyl acetate/hexane to yield α-cyano-4-fluoro-3-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. washwashed with water (3×) and sat. NaCl
  2. customdried
  3. customsolvent is removed
  4. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-2bb22a05aa2143428a6ddfc8b696f31a
Source dataset
uspto-grants-1980_09
Patent number
US04225533

Reaction notes

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