Water → 4-Chloro-2-fluoro-5-methoxybenzyl chloride

HRID 1003989Notes

Reaction equation

HRID 1003989 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].CO[CH2:13][Cl:14].O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][C:5]([CH2:13][Cl:14])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 27735802-Chloro-4-fluoroanisole

Product 1

HCID 184083444-Chloro-2-fluoro-5-methoxybenzyl chlorideYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24193Titanium TetrachlorideSolvent

Procedure

17.6 g (0.11 mol) of 2-chloro-4-fluoroanisole was dissolved in a dichloromethane solution of 1N titanium tetrachloride, and 88.3 g (1.10 mol) of methoxymethyl chloride was dropwise added thereto at room temperature, followed by stirring at room temperature for 5 hours. after completion of the reaction, the reaction solution was poured into water, followed by stirring at room temperature for 2 hours, and then the aqueous phase was removed. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. Then, the obtained residue was purified by silica gel column chromatography to obtain 15.5 g (yield: 68%) of the desired product.

Workup

  1. additionwas dropwise added
  2. customat room temperature
  3. customafter completion of the reaction
  4. stirringby stirring at room temperature for 2 hours
  5. customthe aqueous phase was removed
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f6c72ed51d9745e391b1b72d0d459a90
Source dataset
uspto-grants-2000_04
Patent number
US06048823

Reaction notes

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