Thionyl Chloride → 5-Bromo-6-fluorobenzo[c][1,2,5]thiadiazole

4-Bromo-5-fluorobenzene-1,2-diamine (500 mg, 2.4 mmol) was dissolved in 20 mL chloroform, treated in portions with thionyl chloride (580 mg, 4.9 mmol) and heated to reflux for 20 h. After cooling the mixture was diluted with 60 mL ethyl acetate, washed with 15 mL water, 15 mL saturated NaCl, dried (Na2SO4) and concentrated under vacuum. The material was chromatographed on silica with a 0-30% ethyl acetate-hexane gradient to give the title compound as a white solid (425 mg, 76%): mp 79-82° C.; 1H NMR (400 MHz, CDCl3) δ 8.33 (d, J=6.7 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −102.91; EIMS m/z 232.

1. temperatureheated
2. temperatureto reflux for 20 h
3. temperatureAfter cooling the mixture
4. washwashed with 15 mL water, 15 mL saturated NaCl
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated under vacuum
7. customThe material was chromatographed on silica with a 0-30% ethyl acetate-hexane gradient

ORD 기록

ord-78d1a511660b40378deceba115a73358

출처 데이터셋

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09006250B2