Réaction #1154032

Équation de réaction

n-hexanol

sodium hydride

2-fluoro-5-bromobenzyl bromide

→

1-[2-fluoro-5-bromobenzyloxy]hexane

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe resulting mixture was stirred at ambient temperature for six hours
2. 2
   AutreThe reaction mixture was partitioned between 1 M potassium carbonate/brine (1/1) and diethyl ether
3. 3
   LavageThe organic fraction was washed with brine six times
4. 4
   SéchageThe organic fraction was dried over sodium sulfate
5. 5
   AutreThe solvents were removed in vacuo
6. 6
   AutreThe title intermediate was further purified by liquid chromatography

Mode opératoire

In a 100 ml flask, under a nitrogen atmosphere, n-hexanol (1.44 ml, 11.5 mmol) was dissolved in N,N-dimethylformamide (35 ml). To this solution sodium hydride (60%, 521 mg, 13.0 mmol) was added and the resulting mixture was stirred for ten minutes. To the reaction mixture 2-fluoro-5-bromobenzyl bromide (2.054, 7.67 mmol) was added and the resulting mixture was stirred at ambient temperature for six hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between 1 M potassium carbonate/brine (1/1) and diethyl ether. The organic fraction was washed with brine six times. The organic fraction was dried over sodium sulfate. The solvents were removed in vacuo. The title intermediate was further purified by liquid chromatography.

Source