반응 #317633

반응 방정식

sodium hypochlorite

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanol

4-methoxy-TEMPO

potassium bromide

→

title compound

1-(5,6-DiChloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

용매

water

ethyl acetate

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGto stir for 15 min.
3. 3
   workup.STIRRINGstirred for 15 min
4. 4
   기타the layers were separated
5. 5
   추출the aqueous layer was extracted with ethyl acetate (3×30 mL)
6. 6
   세척washed with water (30 mL) and brine (40 mL)
7. 7
   건조dried over Na2SO4
8. 8
   농축The filtrate was concentrated in vacuo
9. 9
   기타purified by column chromatography (SiO2; 100% ether)

실험 절차

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanol (0.29 g; 1.00 mmole), 4-methoxy-2,2,6,6-tetramethyl-1-piperdinyloxy free radical (4-methoxy-TEMPO free radical; 4.4 mg; 0.03 mmoles) and potassium bromide (KBr; 13 mg; 0.11 mmoles) were dissolved in THF (2.9 mL). The reaction mixture was stirred while cooled to −10° C., after 10 min. a sodium hypochlorite solution (bleach; 10-13% aqueous; 2.10 mL; 3.53 mmoles) was added and allowed to stir for 15 min., then warmed to room temperature and stirred for 15 min. The reaction mixture was diluted with water (20 mL) and ethyl acetate (30 mL), the layers were separated and the aqueous layer was extracted with ethyl acetate (3×30 mL). The extracts were combined and washed with water (30 mL) and brine (40 mL), then dried over Na2SO4. The filtrate was concentrated in vacuo and purified by column chromatography (SiO2; 100% ether) to yield the title compound as a light yellow solid.

출처