Sodium hydride → HCID 14517065, compound

HRID 1904972Notes

Reaction equation

HRID 1904972 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:13]([F:16])([F:15])[F:14])[CH2:11][OH:12])=[CH:6][CH:5]=1.[O:17]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[O:17]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][O:12][CH2:11][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[C:13]([F:14])([F:15])[F:16])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 14517052HCID 14517052, compound

Product 1

HCID 14517065HCID 14517065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 135 mg of sodium hydride (60% oil dispersion) was added to 20 ml of dry THF. A solution of 0.30 g or 2-(4-chlorophenyl)3,3,3-trifluoropropanol and 0.34 g of 3-phenoxybenzyl bromide in 20 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/toluene (2:1) mixture] to obtain 250 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-a7be1b4a47b047579250eb1b01de4f08
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

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