Cesium fluoride → HCID 20036689, compound

HRID 1904976Notes

Reaction equation

HRID 1904976 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]([F:14])([F:13])[F:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.O([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br)C1C=CC=CC=1.[F-].[Cs+]>COCCOCCOC>[C:2]1([C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH2:25][O:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:11]([F:12])([F:13])[F:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 20036620HCID 20036620, compound

Product 1

HCID 20036689HCID 20036689, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Under a nitrogen atmosphere, 0.50 g of 2-(4-fluorophenyl)-3,3,3-trifluoropropanol and 0.63 g of 3-phenoxybenzyl bromide was dissolved in 15 ml of dry diethyleneglycol dimethylether. Into the solution, 1.83 g of dry cesium fluoride was added at room temperature, and the reaction solution was stirred at room temperature for 48 hours. Thereafter, the reaction solution 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 preparative thin-layer chromatography on silica gel to obtain αmg of the desired compound.

Workup

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

Sources & evidence

ORD record
ord-2555e011882e465fa4f4d72c3fc2b5e6
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

Loading…