Carbon tetrabromide → 4-Bromo-2-(bromomethyl)-1-fluorobenzene

In a 250 ml round bottom flask, under a nitrogen atmosphere, 2-fluoro-5-bromobenzyl alcohol (5.85 g, 28.5 mmol) was dissolved in diethy ether (125 ml). To this solution triphenylphosphine (9.73 g, 37.1 mmol) and carbon tetrabromide (12.30 g, 37.1 mmol) were added. The resulting mixture was stirred at ambient temperature for about three hours. The progress of the reaction was monitored by thin layer chromatography. The mixture was then stirred at ambient temperature for about 19 additional hours. The reaction mixture was filtered and washed with cold diethyl ether. The filtrate was evaporated, yielding a light yellow oil. The oil was further purified by chromatography on a silica gel with hexanes. The desired fractions were purified by evaporation to yield 5.8 grams of the desired title intermediate. The material slowly crystallized upon standing.

1. stirringThe mixture was then stirred at ambient temperature for about 19 additional hours
2. filtrationThe reaction mixture was filtered
3. washwashed with cold diethyl ether
4. customThe filtrate was evaporated
5. customyielding a light yellow oil
6. customThe oil was further purified by chromatography on a silica gel with hexanes
7. customThe desired fractions were purified by evaporation

ORD record

ord-6106027def1f48f59d1de82d9f8cf9a6

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1