(Diethylamino)sulfur trifluoride → 1-Bromo-3-(4-fluorobut-1-ynyl)benzene

Temperature

0 °C

A solution of 1.5 gm (6.67 mmol) of 4-(3-bromophenyl)but-3-yn-1-ol in CH2Cl2 at 0° C. was treated with 2.0 mL (15.3 mmol) of DAST, stirred at 0° C. for 1 h, allowed to warm to room temperature for 1 h, poured into saturated sodium bicarbonate and extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the resultant concentrate on silica gel with a gradient of 0% to 24% EtOAc-hexanes gave 1-Bromo-3-(4-fluoro-but-1-ynyl)benzene as a volatile liquid, 0.96 gm (64% yield); 1H NMR (400 MHz, CDCl3) δ: 2.82 (dt, 2H, J=6.6, 19.8 Hz), 4.56 (dt, 2H, J=6.6,46.4 Hz), 7.14 (t, 2H, J=7.9 Hz), 7.31 (m, 1H), 7.41 (m, 1H), 7.55 (t, 1H, J=1.7 Hz).

1. temperatureto warm to room temperature for 1 h
2. extractionextracted with EtOAc
3. washThe combined extracts were washed sequentially with water and brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. concentrationChromatography of the resultant concentrate on silica gel with a gradient of 0% to 24% EtOAc-hexanes

ORD record

ord-99ffb0a02dac4ab3ad52c77f7a062294

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423158B2