Hydrogen Bromide → (S)-2-bromo-1-(tetrahydrofuran-2-yl)ethanone

Temperature

0 °C

To a 250-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was added a solution of (diazomethyl)trimethylsilane (20 mL, 2 M in hexane) in ether (150 mL). A solution of (S)-tetrahydrofuran-2-carbonyl chloride (compound 257.1, 5.00 g, 37.2 mmol, 1.00 equiv) in ether/DCM (25/10 mL) was added dropwise at 0° C. and stirred for 20 min at 0° C. Hydrogen bromide (48%) (8 mL, 1.50 equiv) was added dropwise. The resulting solution was stiffed for 30 min at 10° C., then washed with 2×100 mL of water and 1×50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:50) as eluent to furnish 2.50 g (35%) of (S)-2-bromo-1-(tetrahydrofuran-2-yl)ethanone as a yellow oil.

1. customTo a 250-mL three neck round-bottom flask, which was purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. additionwas added a solution of (diazomethyl)trimethylsilane (20 mL, 2 M in hexane) in ether (150 mL)
4. waitThe resulting solution was stiffed for 30 min at 10° C.
5. washwashed with 2×100 mL of water and 1×50 mL of brine
6. dry with materialThe mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified

ORD record

ord-b1ec1ae721a44526bc798637af342133

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2