Methyl iodide → 1-Methoxy-4-(2-fluoro-5-bromobenzyloxy)butane

Temperature

-78 °C

A solution of 4-(2-fluoro-5-bromobenzyloxy)butanol (897 mg, 3.24 mmol) in tetrahydrofuran (22 ml) was cooled to −40° C. and then treated with potassium t-butoxide (3.56 ml of a 1 M solution in tetrahydrofuran, 3.56 mmol). The resulting orange solution was stirred for thirty minutes, cooled to −78° C. and treated with methyl iodide (0.40 ml, 6.48 mmol). The reaction was warmed to 0° C. and stirred for 1.5 hours. The reaction mixture was then partitioned between methylene chloride and saturated sodium bicarbonate. The organic fraction was dried over sodium sulfate, and the solvents were removed in vacuo. The desired title intermediate was further purified by high performance liquid chromatography to yield 687 mg (73%) as a clear oil.

1. temperatureThe reaction was warmed to 0° C.
2. stirringstirred for 1.5 hours
3. customThe reaction mixture was then partitioned between methylene chloride and saturated sodium bicarbonate
4. dry with materialThe organic fraction was dried over sodium sulfate
5. customthe solvents were removed in vacuo
6. customThe desired title intermediate was further purified by high performance liquid chromatography
7. customto yield 687 mg (73%) as a clear oil

ORD record

ord-a49ef8b3f1ec4515bc3237726132983d

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1