Реакция #710546

Уравнение реакции

2-(trifluoromethyl) aniline

pyridine

4-bromobenzene sulfonyl chloride

→

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

Выход 48.4%

Растворители

DCM

DCM

Условия реакции

Обработка

1. 1
   Промывкаwashed with 1N HCl, sat. NaHCO3, water and brine
2. 2
   Сушкаdried over Na2SO4
3. 3
   Концентрированиеconcentrated under vacuum
4. 4
   ДругоеPurification by silica gel column chromatography (0-20% EtOAc in cyclohexane)
5. 5
   Другоеtriturating with pentane

Методика

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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