Reaction #58861

Reaction equation

ammonium chloride

2-fluoroethanol

sodium hydride

3-bromobenzylbromide

→

1-bromo-3-(2-fluoroethoxymethyl)benzene

Yield 58.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGstirred for 15 min. at room temperature
2. 2
   workup.STIRRINGstirred for 1 h
3. 3
   Extractionextracted with ether
4. 4
   Washwashed sequentially with water and brine
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by flash chromatography on silica gel, 20:1 hexane/ ethyl acetate as eluent

Procedure

A mixture of sodium hydride [60% in oil] (343, mg, 8.6 mmol) and THF at −5° C. was treated via a syringe with a solution of 2-fluoroethanol in THF over a 1 min. period, stirred for 2 min., warmed to room temperature, stirred for 15 min. at room temperature, treated with 3-bromobenzylbromide (2.5 g, 11.7 mmol), stirred for 1 h, poured into saturated ammonium chloride and extracted with ether. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, 20:1 hexane/ ethyl acetate as eluent, to afford 1-bromo-3-(2-fluoroethoxymethyl)benzene as a yellow oil, 1 g (58% yield), 1H NMR (DMSO-d6) δ 3.6 (dxt, 2H); 4.5 (dxt, 2H); 4.4 (s, 2 H); 7.3 (m, 2H); 7.5 (m, 2H); MS [(+)ESI] m/z 219 [M−H]+.

Source