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

HRID 8205

Reaction equation

HRID 8205 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

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1004Phosphoric AcidHCID 94501-Fluoronaphthalene

Product 1

HCID 156574171-(Chloromethyl)-4-fluoronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. extractionextracted three times with dichloromethane
  2. washwashed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-eb6b605148f94f1c8e3a24b3c564aca0
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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