Réaction #1833223

Équation de réaction

1-butanethiol

2-Bromo-6-fluorophenol

potassium carbonate

sodium hydroxide

1,2-dibromo-tetrafluoroethane

→

title compound

Rendement 76.5%

1-Bromo-2-(2-bromo-1,1,2,2-tetrafluoroethoxy)-3-fluorobenzene

Rendement 76.5%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Extractionextracted three times with diethyl ether (80 mL portions)
3. 3
   LavageThe combined extracts were washed with water (15 mL), 2.0 M NaOH (45 mL)
4. 4
   Séchagedried (Na2SO4)
5. 5
   Concentrationconcentrated by rotary evaporation
6. 6
   AutreThe material was purified by silica gel chromatography
7. 7
   Lavageeluting with hexane

Mode opératoire

2-Bromo-6-fluorophenol (10.2 g, 53 mmol), potassium carbonate (7.3 g, 53 mmol), 1,2-dibromo-tetrafluoroethane (21 g, 80 mmol) and 1-butanethiol (1.1 g, 12 mmol) were combined in dry N,N-dimethylformamide (75 mL) and heated to 50° C. in a stirred pressure reactor. After cooling, the contents were mixed with 1.0 M sodium hydroxide (NaOH; 100 mL) and extracted three times with diethyl ether (80 mL portions). The combined extracts were washed with water (15 mL), 2.0 M NaOH (45 mL), dried (Na2SO4) and concentrated by rotary evaporation. The material was purified by silica gel chromatography eluting with hexane to afford the title compound as a clear liquid (15 g, 76%): 1H NMR (400 MHz, CDCl3) δ 7.48-7.39 (m, 1H), 7.22-7.14 (m, 2H); EIMS m/z 368.

Source