反応 #1833240

反応方程式

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

thiophosgene

Sodium hydroxide

→

title compound

収率 62.1%

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

収率 62.1%

溶媒

chloroform

ethyl acetate

反応条件

後処理

1. 1
   workup.WAITAfter 1 h
2. 2
   その他the chloroform was removed under vacuum
3. 3
   workup.ADDITIONthe pH was adjusted to 2 by addition of 6 M HCl
4. 4
   その他The solid that was formed
5. 5
   洗浄washed with saturated NaCl (30 mL)
6. 6
   乾燥dried (Na2SO4)
7. 7
   その他evaporated
8. 8
   その他The material was purified by flash chromatography

実験手順

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.

出典