1,4-Butanediol → 4-(2-Fluoro-5-bromobenzyloxy)butanol

A solution of 1,4-dihydroxybutane (4.0 ml, 45.13 mmol) in N,N-dimethylformamide (62 ml) was treated with sodium hydride (1.98 g of a 60% solution, 49.63 mmol), and stirred for about 50 minutes at ambient temperature. The resulting mixture was cooled to 0° C. and treated with 2-fluoro-5-bromobenzyl bromide (3.0 g, 11.28 mmol). The reaction mixture was then stirred for four hours at ambient temperature. The reaction was quenched with water. The aqueous fraction was extracted with methylene chloride. The organic fractions were combined, and dried over sodium sulfate. The solvents were removed in vacuo. The desired title intermediate was further purified by high performance liquid chromatography.

1. temperatureThe resulting mixture was cooled to 0° C.
2. stirringThe reaction mixture was then stirred for four hours at ambient temperature
3. customThe reaction was quenched with water
4. extractionThe aqueous fraction was extracted with methylene chloride
5. dry with materialdried over sodium sulfate
6. customThe solvents were removed in vacuo
7. customThe desired title intermediate was further purified by high performance liquid chromatography

ORD record

ord-96ffe5c3cac14f118bd24bd99d6196d6

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1