Water → 1-(Chloromethyl)-4-(fluoromethyl)benzene

HRID 889142

Reaction equation

HRID 889142 reaction equation
[Cl:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.O.C(=O)([O-])O.[Na+].CN(S(F)(F)[F:21])C>ClCCl>[Cl:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][F:21])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123203Sulfur, trifluoro(N-methylmethanaminato)-HCID 516892Sodium BicarbonateHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 189264181-(Chloromethyl)-4-(fluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 4-(chloromethyl)benzyl alcohol (5.00 g) in dichloromethane (90 ml), dimethylaminosulfur trifluoride (8.28 ml) was added at room temperature and the mixture was stirred for one day. Water was added to the reaction mixture, and then a saturated aqueous solution of sodium hydrogencarbonate was added and extraction was performed with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.94 g).

Workup

  1. additionwas added at room temperature
  2. extractionextraction
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f012dcd74e9640939620c4371adbe3ec
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Linked notes

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