Reaction #42391

Reaction equation

N-methylbutylamine

triethylamine

methyl 3-bromo-5-(hydroxymethyl)benzoate

methanesulfonyl chloride

→

title compound

Methyl 3-bromo-5-{[butyl(methyl)amino]methyl}benzoate

Solvents

methylene chloride

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   workup.STIRRINGstirred at room temperature for 16 h
3. 3
   ConcentrationThe solution is concentrated under reduced pressure
4. 4
   Otherthe residue is purified by flash column chromatography (silica, 8% ethyl acetate/hexanes)

Procedure

To a solution of methyl 3-bromo-5-(hydroxymethyl)benzoate (4.1 g, 16.8 mmol) in anhydrous methylene chloride (35 mL) at −30° C. is added methanesulfonyl chloride (1.82 mL, 23.5 mmol) followed by triethylamine (4.7 mL, 33.6 mmol). The reaction mixture is stirred for 45 min at 0° C., and then filtered. The filtrate is added to N-methylbutylamine (6 mL, 50.4 mmol) and stirred at room temperature for 16 h. The solution is concentrated under reduced pressure, and the residue is purified by flash column chromatography (silica, 8% ethyl acetate/hexanes) to give the title compound. ESI MS m/z 314.1 [M+H]+.

Source