Sodium hydride → 2-(3-Chloro-4-ethoxyphenyl)-3,3,3-trifluoropropyl 3-(4-fluorophenoxy)benzyl ether

HRID 1904977Notes

Reaction equation

HRID 1904977 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:13]([C:16]([F:19])([F:18])[F:17])[CH2:14][OH:15])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12].[F:20][C:21]1[CH:35]=[CH:34][C:24]([O:25][C:26]2[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=2)[CH2:29]Br)=[CH:23][CH:22]=1>C1COCC1>[F:20][C:21]1[CH:35]=[CH:34][C:24]([O:25][C:26]2[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=2)[CH2:29][O:15][CH2:14][CH:13]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH3:12])=[C:4]([Cl:3])[CH:5]=2)[C:16]([F:17])([F:18])[F:19])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27374563-(4-Fluorophenoxy)benzyl BromideHCID 200366852-(3-Chloro-4-ethoxyphenyl)-3,3,3-trifluoropropanol

Product 1

HCID 145808152-(3-Chloro-4-ethoxyphenyl)-3,3,3-trifluoropropyl 3-(4-fluorophenoxy)benzyl etherYield 35.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 60 mg of sodium hydride (60% oil dispersion) was added to 10 ml of dry THF. A solution of 0.41 g of 2-(3-chloro-4-ethoxyphenyl)-3,3,3-trifluoropropanol and 1.43 g of 3-(4-fluorophenoxy)benzyl bromide in 10 ml of dry THF was then added with ice-cooling, and the reaction solution was stirred with ice-cooling for 1 hour and at room temperature for 12 hours. Thereafter, the reaction mixture was poured into dilute HCl-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure, and the residue was subjected to column chromatography on silica gel [eluted with n-hexane/ethyl acetate (40:1) mixture] to obtain 255 mg of the desired compound.

Workup

  1. temperaturecooling
  2. extractionextracted twice with diethyl ether
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-15c3f46d6ff44ef7b55f69dc6106e831
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

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