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

HRID 354700Notes

Reaction equation

HRID 354700 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=6 Hz, CH3); 1.05(3H,d of d, J=6 Hz and J=2 Hz, CH3); 2.34(1H, m, --CH(CH3)2); 3.29 (1H, d, J=10 Hz, CH); 7.22(1H, d of d, J=56 Hz and J=2 Hz, 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-3c6f068a9ec345f58cffee4036939934
Source dataset
uspto-grants-1983_03
Patent number
US04376784

Reaction notes

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