반응 #710546

반응 방정식

2-(trifluoromethyl) aniline

pyridine

4-bromobenzene sulfonyl chloride

→

4-bromo-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide

수율 48.4%

용매

DCM

DCM

반응 조건

후처리

1. 1
   세척washed with 1N HCl, sat. NaHCO3, water and brine
2. 2
   건조dried over Na2SO4
3. 3
   농축concentrated under vacuum
4. 4
   기타Purification by silica gel column chromatography (0-20% EtOAc in cyclohexane)
5. 5
   기타triturating with pentane

실험 절차

A solution of 2-(trifluoromethyl) aniline (693 mg, 4.30 mmol) and pyridine (438 μL, 5.87 mmol) in DCM (40 mL) was treated with 4-bromobenzene sulfonyl chloride (1.0 g, 3.91 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1N HCl, sat. NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-20% EtOAc in cyclohexane) and triturating with pentane gave 4-bromo-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (719 mg, 48% yield) as a colourless crystalline solid. 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.2 Hz, 1H), 7.65-7.47 (m, 6H), 7.29-7.20 (m, 1H), 6.85 (br s, 1H), LCMS (m/z, Method A) ES+ 380.0 [M+1]+.

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