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

HRID 1860660Notes

Reaction equation

HRID 1860660 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]>>[Cl:3][CH2:13][C:8]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:6]([F:5])[CH:7]=1

Participants

3

Reactant 2

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

Product 1

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

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) 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 washed with saturated NaHCO3, brine and dried with Na0.2SO4. Ether was evaporated and the residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9) to give a clear 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 washed with saturated NaHCO3, brine
  5. customdried with Na0.2SO4
  6. customEther was evaporated
  7. customthe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9)
  8. customto give a clear liquid in 10.5 g

Sources & evidence

ORD record
ord-8c5ecd99956f45fcb884e9c31c6a50b6
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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