Hydrogen Bromide → 2-Bromo-1-(oxan-4-yl)ethan-1-one

Thionyl chloride (2 mL, 27 mmol) was added to tetrahydro-pyran-4-carboxylic acid (1.1 g, 8.4 mmol) at 10° C. The mixture was warmed to ambient temperature and stirred for 2 h. Excess thionyl chloride was evaporated and the residue co-distilled with toluene to remove the traces of thionyl chloride. The resulting crude acid chloride was dissolved in dry acetonitrile (3 mL) and cooled to 0° C. Trimethylsilyl diazomethane (12.6 mL, 25.3 mmol) was added and the reaction mixture was stirred at ambient temperature for 2 h. It was then cooled to −10° C. and a solution of 15% HBr in acetic acid (2 mL) was added. The mixture was stirred at room temperature for 1 h then quenched with saturated sodium bicarbonate solution and extracted with ether (3×20 mL). The combined ether extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-bromo-1-(tetrahydro-pyran-4-yl)-ethanone (620 mg, 35%) as an oil.

1. customExcess thionyl chloride was evaporated
2. customthe residue co-distilled with toluene to remove the traces of thionyl chloride
3. dissolutionThe resulting crude acid chloride was dissolved in dry acetonitrile (3 mL)
4. temperaturecooled to 0° C
5. stirringthe reaction mixture was stirred at ambient temperature for 2 h
6. temperatureIt was then cooled to −10° C.
7. stirringThe mixture was stirred at room temperature for 1 h
8. customthen quenched with saturated sodium bicarbonate solution
9. extractionextracted with ether (3×20 mL)
10. washThe combined ether extracts were washed with brine
11. dry with materialdried over anhydrous sodium sulfate
12. concentrationconcentrated in vacuo

ORDレコード

ord-14c99293b6284365afb933e1cf0a3daf

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08524705B2