Reaction #710540

Reaction equation

HCl

3-chloroaniline

(4-bromo-phenyl)-methanesulfonyl chloride

pyridine

→

C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide

Yield 32.3%

Solvents

DCM

Conditions

Workup

1. 1
   Extractionextracted with DCM
2. 2
   Filtrationfiltered through a separator
3. 3
   Concentrationconcentrated
4. 4
   Otherdry loaded onto silica
5. 5
   Otherpurified by silica gel column chromatography (0-100% DCM in cyclohexane)

Procedure

To a solution of (4-bromo-phenyl)-methanesulfonyl chloride (1.4 g, 5.2 mmol) in DCM (20 mL) at room temperature was added pyridine (1.26 mL, 15.6 mmol) followed by 3-chloroaniline (1.1 mL, 10.4 mmol) and the reaction was stirred at room temperature for 3 hours. 1 M aqueous HCl was added and then extracted with DCM, filtered through a separator, concentrated, dry loaded onto silica and purified by silica gel column chromatography (0-100% DCM in cyclohexane) to give C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide (0.61 g, 1.68 mmol). 1H NMR (300 MHz, CDCl3): δ 7.49 (d, 2 H), 7.26 (m, 1 H), 7.13-7.15 (m, 4 H), 6.96-6.98 (m, 1 H), 6.31 (s, 1 H), 4.31 (s, 2 H).

Source