Water → 3-(2-Fluoroethoxy)benzyl benzyl ether

HRID 1583593Notes

Reaction equation

HRID 1583593 reaction equation
[H-].[Na+].[F:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][OH:11].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>O1CCCC1>[CH2:15]([O:11][CH2:10][C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][CH2:5][CH2:4][F:3])[CH:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 53719951(3-(2-Fluoroethoxy)phenyl)methanol

Product 1

HCID 133676633-(2-Fluoroethoxy)benzyl benzyl etherYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.24 g; 60% in oil) was suspended in 30 ml of dry tetrahydrofuran, and then 1.0 g of 3-(2-fluoroethoxy)benzyl alcohol was added. The mixture was stirred at 50° to 60° C. for 30 minutes, and 1.7 g of benzyl bromide was added. The mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (50 g) column chromatography (developing solvent: toluene) to give 1.2 g of 3-(2-fluoroethoxy)benzyl benzyl ether.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customToluene was evaporated under reduced pressure
  7. customThe resulting crude ether was purified by silica gel (50 g) column chromatography (developing solvent: toluene)

Sources & evidence

ORD record
ord-ddde18a5bd6c4d4cabd6a0801a80876a
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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