Reaction #710546

Reaction equation

2-(trifluoromethyl) aniline

pyridine

4-bromobenzene sulfonyl chloride

→

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

Yield 48.4%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   Washwashed with 1N HCl, sat. NaHCO3, water and brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Concentrationconcentrated under vacuum
4. 4
   OtherPurification by silica gel column chromatography (0-20% EtOAc in cyclohexane)
5. 5
   Othertriturating with pentane

Procedure

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]+.

Source