Acetic Acid → 1-(Chloromethyl)-4-fluoronaphthalene

Reaction equation

[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C=O.P(=O)(O)(O)O.[ClH:19].[C:20](O)(=O)C>O>[Cl:19][CH2:20][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([F:1])=[CH:3][CH:4]=1

Participants

Reactant 5

HCID 176Acetic Acid

HCID 313Hydrochloric Acid

HCID 712Formaldehyde

HCID 1004Phosphoric Acid

HCID 94501-Fluoronaphthalene

Product 1

HCID 156574171-(Chloromethyl)-4-fluoronaphthalene

Reagents, catalysts & solvents 1

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.