Dichloromethane → 2-(Chloromethyl)-1,3-difluoro-4-methoxybenzene

HRID 1486299Notes

Reaction equation

HRID 1486299 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[CH2:11]O.[Cl:13]CCl>S(Cl)(Cl)=O>[Cl:13][CH2:11][C:3]1[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[CH:5][C:4]=1[F:10]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 52448622,6-Difluoro-3-methoxybenzyl alcohol

Product 1

HCID 834101602-(Chloromethyl)-1,3-difluoro-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 120 mg (0.689 mmol) of 2,6-difluoro-3-methoxyphenyl)methanol from Example 132A in 3 ml of dichloromethane and 1 ml of thionyl chloride was stirred at room temperature overnight. The solvent was evaporated off under reduced pressure and the residue was purified by flash chromatography using a prepacked silica gel cartridge (eluent:cyclohexane-ethyl acetate 10:1 to 1:1), which gave 50 mg (38% of theory) of the target compound.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue was purified by flash chromatography
  3. customgave 50 mg (38% of theory) of the target compound

Sources & evidence

ORD record
ord-49b063f191724ed6b57e4918eb30b772
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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