Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 2-Bromo-1-(2-chloroethoxy)-4-fluorobenzene

Temperature

50 °C

To a solution of toluene-4-sulfonic acid 2-chloroethyl ester (2.80 g, 11.93 mmol) in anhydrous N,N-dimethylformamide (10 ml) was added 2-bromo-4-fluorophenol (2.73 g, 14.30 mmol), and potassium carbonate (3.30 g, 23.90 mmol). The resulting solution was then heated at 50° C. with stirring for 6 hours. After cooling to room temperature, the reaction mixture was diluted with sodium hydroxide (1M aqueous solution, 30 ml) and tert-butyldimethyl ether (50 ml) was added. The layers were separated and the organic extract was washed with saturated brine solution (30 ml), prior to being dried over anhydrous MgSO4 (s), filtered and evaporated in vacuo. Purification by column chromatography eluting with ethyl acetate:heptane 1:99 to 10:90 afforded the title compound as a colourless oil (1.50 g, 50%).

1. temperatureAfter cooling to room temperature
2. additionwas added
3. customThe layers were separated
4. extractionthe organic extract
5. washwas washed with saturated brine solution (30 ml)
6. dry with materialto being dried over anhydrous MgSO4 (s)
7. filtrationfiltered
8. customevaporated in vacuo
9. customPurification by column chromatography
10. washeluting with ethyl acetate:heptane 1:99 to 10:90

ORD record

ord-a1156f02ed1748ab858b7816fc1a6c15

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2