Sodium Chloride → 1,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-ene

HRID 329487Notes

Reaction equation

HRID 329487 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[F:15])[CH2:10][OH:11])=[CH:4][CH:3]=1.[H-].[Na+].[F:20][C:21]([F:35])([F:34])[C:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)=[CH:23]Cl.[Cl-].[Na+]>CN(C)C=O.O>[F:20][C:21]([F:34])([F:35])[C:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)=[CH:23][O:11][CH2:10][C:9]1[CH:12]=[CH:13][C:14]([F:15])=[C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:8]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 159177183-(4-Chlorophenoxy)-4-fluorobenzyl alcoholHCID 540539251,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-chloroprop-2-ene

Product 1

HCID 537269141,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-eneYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
-10 °C

Procedure

A solution of 3-(4-chlorophenoxy)-4-fluorobenzyl alcohol (6.3 g) in N,N-dimethylformamide (20 cm3) was added to a stirred suspension of sodium hydride (1.2 g of a 50% dispersion in oil) in N,N-dimethylformamide. After 30 minutes, this mixture was added to a stirred solution of EZ-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-chloroprop-2-ene (5 g) in N,N-dimethylformamide (25 cm3) at a temperature maintained at -10° C. during the addition. After 45 minutes the reaction mixture was poured into water (150 cm3) and sodium chloride added. The products were extracted into diethyl ether (4×100 cm3), and the combined organic layers were dried over anhydrous sodium sulphate and concentrated by evaporation under reduced pressure. The crude residue was purified by column chromatography on a silica gel support, eluted with n-hexane containing 6% by volume diethyl ether, to give 1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-ene (6 g).

Workup

  1. additionadded
  2. extractionThe products were extracted into diethyl ether (4×100 cm3)
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulphate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe crude residue was purified by column chromatography on a silica gel support
  6. washeluted with n-hexane containing 6% by volume diethyl ether

Sources & evidence

ORD record
ord-13297b6953d7406893b193ae19e02f35
Source dataset
uspto-grants-1990_01
Patent number
US04891450

Reaction notes

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