Thionyl Chloride → 4-(Chloromethyl)-2-fluoro-1-methylbenzene

HRID 1860651Notes

Reaction equation

HRID 1860651 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:7]=[C:8]([CH2:13]O)[CH:9]=[CH:10][C:11]=1[CH3:12]>CCOCC>[Cl:3][CH2:13][C:8]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:6]([F:5])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2774590(3-Fluoro-4-methylphenyl)methanol

Product 1

HCID 186241474-(Chloromethyl)-2-fluoro-1-methylbenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (0.892 g, 7.5 mmol) was added to a solution of the product of STEP 1 (1.0 g, 6.4 mmol) in 10 ml ether dropwise at 0° C. After 30 min, the reaction was quenched with crushed ice carefully, and diluted with H2O. The product was extracted with ether. The organic layer was washed with saturated NaHCO3 solution, brine, dried with Na2SO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9) to give a colorless liquid in 10.5 g. NMR spectra of the product were consistent for the proposed structure.

Workup

  1. customthe reaction was quenched with crushed ice carefully
  2. additiondiluted with H2O
  3. extractionThe product was extracted with ether
  4. washThe organic layer was washed with saturated NaHCO3 solution, brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9)
  8. customto give a colorless liquid in 10.5 g

Sources & evidence

ORD record
ord-ecf6119a27da40c481bd79cb57489a5c
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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