Reaction #4565

Reaction equation

3-chloro-4-fluoroaniline

pyridine

2-chloroacetyl chloride

→

N-(2-chloroacetyl)-3-chloro-4-fluoroaniline

Yield 88.0%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe resulting solution was cooled to ca 0° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 5 hours
3. 3
   Extractionit was extracted twice with 100 ml
4. 4
   DryingThe resulting toluene solution was dried
5. 5
   Concentrationit was concentrated in vacuo
6. 6
   Otherto give 32.6 g

Procedure

To 130 ml. of toluene was added, with stirring, 24.0 g. (0.165 mole) of 3-chloro-4-fluoroaniline and 13.5 ml. (0.166 mole) of pyridine. The resulting solution was cooled to ca 0° C. and 13.2 ml. (0.166 mole) of 2-chloroacetyl chloride was added. The reaction mixture was stirred at room temperature for 5 hours and then it was extracted twice with 100 ml. of 1N hydrochloric acid, followed by 100 ml. of saturated sodium chloride solution. The resulting toluene solution was dried using magnesium sulfate, and then it was concentrated in vacuo to give 32.6 g. (88% yield) of N-(2-chloroacetyl)-3-chloro-4-fluoroaniline.

Source