Sodium hydride → 2-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-(4-bromophenoxy)benzyl ether

HRID 1904975Notes

Reaction equation

HRID 1904975 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:13][OH:14])=[CH:8][CH:7]=1)[CH3:4].[Br:19][C:20]1[CH:34]=[CH:33][C:23]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[CH2:28]Br)=[CH:22][CH:21]=1>C1COCC1>[Br:19][C:20]1[CH:34]=[CH:33][C:23]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[CH2:28][O:14][CH2:13][CH:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:3][CH3:4])=[CH:11][CH:10]=2)[C:15]([F:16])([F:17])[F:18])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-olHCID 145170553-(4-Bromophenoxy)benzyl bromide

Product 1

HCID 140539892-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-(4-bromophenoxy)benzyl etherYield 30.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 171 mg of sodium hydride (60% oil dispersion) was added to 20 ml of dry THF. A solution of 1.0 g of 2-(4-ethoxyphenyl)-3,3,3-trifluoropropanol and 1.30 g of 3-(4-bromophenoxy)benzyl bromide in 30 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 (50:1) mixture] to obtain 0.58 g 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-281aa55ea39d473b916f0d69f32271fe
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

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