Water → alpha-Fluoro-3-phenoxybenzyl alpha-isopropyl-4-chlorophenylacetate

HRID 894337Notes

Reaction equation

HRID 894337 reaction equation
[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:5]([O-:7])=[O:6])([CH3:3])[CH3:2].[K+].[F:16][CH:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1.O>CN(C)C=O>[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:5]([O:7][CH:17]([F:16])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:19]=1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 13194583alpha-Fluoro-3-phenoxybenzylbromideHCID 23685460Potassium alpha-isopropyl-4-chlorophenylacetate

Product 1

HCID 20507332alpha-Fluoro-3-phenoxybenzyl alpha-isopropyl-4-chlorophenylacetateYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium α-isopropyl-4-chlorophenylacetate (0.91 g) and α-fluoro-3-phenoxy benzyl bromide (1.06 g) in dimethylformamide (10 ml) was stirred at ambient temperature over a period of 2 hours. The reaction mixture was poured into water and the aqueous solution was extracted with diethyl ether. The ether extract was washed with aqueous sodium carbonate solution and was then dried over anhydrous sodium sulfate. The ether was removed by distillation under reduced pressure and the residue chromatographed over silica gel to give α-fluoro-3-phenoxybenzyl α-isopropyl-4-chlorophenylacetate (0.62 g; 37%) as a colourless oil. The product was characterised by pmr spectroscopy. Chemical shift δppm (solvent CDCl3): 0.69(3H, d, J=6Hz, CH3); 1.05(3H, d of d, J=6Hz and J=2Hz, CH3); 2.34(1H, m, --CH(CH3)2); 3.29 (1H, d, J=10Hz, CH); 7.22(1H, d of d, J=56Hz and J= 2Hz, CHF) and c. 7.24(13H, m, aromatic protons).

Workup

  1. extractionthe aqueous solution was extracted with diethyl ether
  2. extractionThe ether extract
  3. washwas washed with aqueous sodium carbonate solution
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe ether was removed by distillation under reduced pressure
  6. customthe residue chromatographed over silica gel

Sources & evidence

ORD record
ord-6fe6199aa5a045ad9efd3530f7f17c09
Source dataset
uspto-grants-1981_08
Patent number
US04283414

Reaction notes

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