반응 #325769

반응 방정식

sodium hydrogen phosphate

sodium sulfite

4-fluoro-benzenesulfonyl chloride

bromoethane

→

1-ethanesulfonyl-4-fluoro-benzene

수율 63.2%

용매

water

water

acetone

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   workup.STIRRINGwas stirred at room temperature for 5 days
3. 3
   추출extracted with ethyl acetate (100 mL×3)
4. 4
   세척The combined organic layers were washed with brine
5. 5
   건조dried over sodium sulfate
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by flash column chromatography (elution with 20% ethyl acetate in petroleum ether)

실험 절차

To a solution of sodium hydrogen phosphate (14.2 g, 0.1 mol) and sodium sulfite (25.2 g, 0.2 mol) in water (200 mL) was added 4-fluoro-benzenesulfonyl chloride (19.5 g, 0.1 mol). After the mixture was stirred at 60° C. overnight, a solution of bromoethane (32.7 g, 0.3 mol) in acetone (20 mL) was added dropwise, followed by the addition of tetrabutylammonium iodide (3.7 g, 0.01 mol) in one portion. The resulting reaction mixture was stirred at room temperature for 5 days, then diluted with water (50 mL), and extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (elution with 20% ethyl acetate in petroleum ether) to afford 1-ethanesulfonyl-4-fluoro-benzene (11.9 g, 63%) as a yellow oil (reference: Arnold, Leggy A. A., et al., Org. Lett, 6 (2004), 3005-3007).

출처