تفاعل #1833240

معادلة التفاعل

5-Bromo-3-fluorobenzene-1,2-diol

thiophosgene

Sodium hydroxide

→

title compound

المردود 62.1%

6-Bromo-4-fluorobenzo[d][1,3]dioxole-2-thione

المردود 62.1%

المذيبات

chloroform

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 1 h
2. 2
   أخرىthe chloroform was removed under vacuum
3. 3
   workup.ADDITIONthe pH was adjusted to 2 by addition of 6 M HCl
4. 4
   أخرىThe solid that was formed
5. 5
   غسيلwashed with saturated NaCl (30 mL)
6. 6
   تجفيفdried (Na2SO4)
7. 7
   أخرىevaporated
8. 8
   أخرىThe material was purified by flash chromatography

الإجراء التجريبي

5-Bromo-3-fluorobenzene-1,2-diol (2.0 g, 9.7 mmol, prepared according to Lu, Hejun; Tang, Peng Cho; Chen, Yiqian; Wang, Shenglan; Wang, Hua; Zhang, Lei; Li, Jun, WO 2011140936 A1) was dissolved in chloroform (25 mL), treated with thiophosgene (1.2 g, 11 mmol) and cooled to 0-5° C. Sodium hydroxide (10% aqueous, 8.9 g, 22 mmol) was added dropwise with vigorous stirring over 30 min. After 1 h, the chloroform was removed under vacuum and the pH was adjusted to 2 by addition of 6 M HCl. The solid that was formed was taken up in ethyl acetate (120 mL), washed with saturated NaCl (30 mL), dried (Na2SO4) and evaporated. The material was purified by flash chromatography using a 0-30% ethyl acetate-hexane gradient to give the title compound as a tan solid (1.5 g, 62%): mp 41-42° C.; 1H NMR (400 MHz, CDCl3) δ 7.35-7.30 (m, 1H), 7.29 (d, J=1.6 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −128.93; EIMS m/z 248/250.

المصدر