Reaction #7835

Reaction equation

4-(bromomethyl)-3-chlorobenzoic acid

NaCN

HCl

→

3-chloro-4-(cyanomethyl)benzoyl chloride

Solvents

DMF

H2O

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to rt
2. 2
   ExtractionThe aqueous mixture was extracted with CH2Cl2 (3×25 mL)
3. 3
   ConcentrationThe combined organic layers were concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONdissolved in MTBE
5. 5
   WashThe organic mixture was washed with H2O and brine (3×25 mL)
6. 6
   Dryingdried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

A suspension of 4-(bromomethyl)-3-chlorobenzoic acid (4.0 g, 16 mmol) in DMF (120 mL) and H2O (40 mL) was treated with NaCN (2.4 g, 49 mmol) and heated to 80° C. for 2 h. The mixture was cooled to rt and acidified with 1N HCl. The aqueous mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were concentrated under reduced pressure and dissolved in MTBE. The organic mixture was washed with H2O and brine (3×25 mL), dried over MgSO4, filtered and concentrated to afford 3-chloro-4-(cyanomethyl)benzoyl chloride.

Source