Reaction #8301

Reaction equation

1-fluoronaphthalene

paraformaldehyde

phosphoric acid

hydrochloric acid

acetic acid

→

title compound

1-Chloromethyl-4-fluoronaphthalene

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted three times with dichloromethane
2. 2
   Washwashed with water and brine
3. 3
   Dryingdried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated

Procedure

A solution of 1-fluoronaphthalene (5.5 g, 37.6 mmol), paraformaldehyde (2.5 g, 83 mmol), glacial acetic acid (3.5 mL), phosphoric acid (2 mL) and concentrated hydrochloric acid (5 mL) is heated at 85° C. for 15 h. The reaction mixture is poured into water and extracted three times with dichloromethane. The organic extracts are combined and washed with water and brine, dried (sodium sulfate), filtered, and evaporated to yield the title compound, 6.53 g (98%, as a yellow solid.

Source