1-Hexanol → HCID 21196153, compound

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.

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

ORD record

ord-75ec35ec50924601a537ba5521708afb

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1