Reaktion #1833240

Reaktionsgleichung

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

thiophosgene

Sodium hydroxide

→

title compound

Ausbeute 62.1%

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

Ausbeute 62.1%

Lösungsmittel

chloroform

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle