Reaction #710547

Reaction equation

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

1-bromo-2-methyl propane

K2CO3

→

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

Yield 69.0%

Solvents

DMF

EtOAc

Conditions

Workup

1. 1
   Washwashed with water (3×) and brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Concentrationconcentrated under vacuum
4. 4
   OtherPurification by silica gel column chromatography (0-15% EtOAc in cyclohexane)
5. 5
   Othertriturating with pentane

Procedure

A mixture of 4-bromo-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (710 mg, 1.87 mmol), 1-bromo-2-methyl propane (305 μL, 2.80 mmol) and K2CO3 (412 mg, 2.99 mmol) in DMF (5 mL) was heated at 90° C. for 18 hours. The cooled mixture was diluted with EtOAc, washed with water (3×) and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-15% EtOAc in cyclohexane) and triturating with pentane gave 4-bromo-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (562 mg, 69% yield) as a colourless crystalline solid. 1H NMR (300 MHz, CDCl3) δ 7.76-7.71 (m, 1H), 7.72-7.55 (m, 2H), 7.57-7.56 (m, 2H), 7.58-7.43 (m, 2H), 7.13-7.09 (m, 1H), 3.53-3.08 (m, 2H), 1.66-1.63 (m, 1H), 0.90 (d, J=6.5 Hz, 3H), 0.81 (d, J=6.7 Hz, 3H), LCMS (m/z, Method A) ES+ 436.0 [M+1]+.

Source