Reaction #710543

Reaction equation

water

4-Fluorobenzyl bromide

4-bromo-N-isobutyl-benzenesulfonamide

NaH

→

4-bromo-N-(4-fluoro-benzyl)-N-isobutyl-benzenesulfonamide

Yield 78.0%

Solvents

dimethylacetamide

Conditions

Workup

1. 1
   Otherreaction
2. 2
   Temperatureheated at 90° C. for 2 hours
3. 3
   workup.WAITThe reaction was left
4. 4
   Temperatureto cool to room temperature
5. 5
   Extractionextracted with DCM
6. 6
   Filtrationfiltered through a phase separator
7. 7
   Concentrationconcentrated
8. 8
   Otherpurified by silica gel column chromatography (0-25% DCM in cyclohexane)

Procedure

To a solution of 4-bromo-N-isobutyl-benzenesulfonamide (0.25 g, 856 μmol) in anhydrous dimethylacetamide (5 mL) was added NaH (60% dispersion in mineral oil, 37.7 mg, 942 μmol) and the mixture was stirred at room temperature for 15 minutes. 4-Fluorobenzyl bromide (117 μL, 942 μmol) was added and reaction heated at 90° C. for 2 hours. The reaction was left to cool to room temperature, water added and then extracted with DCM, filtered through a phase separator, concentrated and purified by silica gel column chromatography (0-25% DCM in cyclohexane) to give 4-bromo-N-(4-fluoro-benzyl)-N-isobutyl-benzenesulfonamide (267 mg, 78%) 1H NMR (300 MHz, CDCl3): δ 7.65-7.66 (m, 4 H), 7.23 (m, 2 H), 6.99 (t, 2 H), 4.27 (s, 2 H), 2.89 (d, 2 H), 1.64 (dt, 1 H), 0.74 (d, 6 H).

Source