Potassium Carbonate → 2-Fluoro-5-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

HRID 28099Notes

Reaction equation

HRID 28099 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+].[K+].CN(C)P(=O)(N(C)C)N(C)C.[F:34][C:35]1[CH:42]=[CH:41][C:40]([O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:39][C:36]=1[CH2:37]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH2:37][C:36]3[CH:39]=[C:40]([O:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:41]=[CH:42][C:35]=3[F:34])=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 145791322-Fluoro-5-phenoxybenzyl bromideHCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 544406292-Fluoro-5-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (2.77 mmol), potassium carbonate (3.25 mmol) and hexamethylphosphoric triamide (HMPT) (3 ml), with stirring and under nitrogen, at RT, is added 2-fluoro-5-phenoxybenzyl bromide (2.77 mmol) in THF. The reaction is stirred at RT for about 48 hours and then worked up by partition between water/ether. The organic phase is washed with water and brine, dried over potassium carbonate, filtered and the solvent is removed from the filtrate. The residue is plated on prep. TLC plates developing with 10% ether/hexane to yield 2-fluoro-5-phenoxybenzyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. stirringThe reaction is stirred at RT for about 48 hours
  2. customby partition between water/ether
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. customthe solvent is removed from the filtrate

Sources & evidence

ORD record
ord-bd1c0c1c5b2d448aa9897a4eb2fd9cf3
Source dataset
uspto-grants-1980_09
Patent number
US04225533

Reaction notes

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