Methyl Ethyl Ketone → HCID 54001202, compound

1-Bromodecane (12.01 g, 48.2 mmol) in butanone (20 ml) was added dropwise to a stirred, refluxing mixture of 4-bromo-3-fluorophenol (1) (9.04 g, 47.4 mmol), potassium carbonate (10.12 g, 73.2 mmol) and butanone (100 ml). The resulting reaction mixture was refluxed for a further 20 hours. The cooled reaction mixture was then filtered to remove the excess potassium carbonate and precipitated potassium bromide. The filtrate was washed with 5% (v/v) sodium hydroxide (2×50 ml) then water (50 ml) and the organic layer then dried (MgSO4), filtered and evaporated under reduced pressure to give a colourless oil which was purified by column chromatography [silica gel: 1:1 dichloromethane-petrol (bp 40°-60° C.)] to give a colourless liquid. This was then dried in vacuo (P2O5, 0.20 mm Hg, RT, 5 h).

1. temperaturerefluxing
2. customThe resulting reaction mixture
3. temperaturewas refluxed for a further 20 hours
4. customThe cooled reaction mixture
5. filtrationwas then filtered
6. customto remove the excess potassium carbonate
7. customprecipitated potassium bromide
8. washThe filtrate was washed with 5% (v/v) sodium hydroxide (2×50 ml)
9. dry with materialwater (50 ml) and the organic layer then dried (MgSO4)
10. filtrationfiltered
11. customevaporated under reduced pressure
12. customto give a colourless oil which
13. customwas purified by column chromatography [silica gel: 1:1 dichloromethane-petrol (bp 40°-60° C.)]
14. customto give a colourless liquid
15. dry with materialThis was then dried in vacuo (P2O5, 0.20 mm Hg, RT, 5 h)

ORD record

ord-2e945f6170c14094abf08278381f8216

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05595682