Thionyl Chloride → 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole

HRID 629390Notes

Reaction equation

HRID 629390 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=2)=[N:3]1.S(Cl)([Cl:17])=O>C1COCC1.O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:17][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 2

HCID 24386Thionyl ChlorideHCID 24229469[4-(1-methyl-1H-pyrazol-3-yl)phenyl]methanol

Product 1

HCID 242294723-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
17 °C

Procedure

To a solution of [4-(1-methyl-1H-pyrazol-3-yl)phenyl]methanol (1.00 g) in THF (15.0 mL) was added dropwise thionyl chloride (0.58 mL) under ice-cooling, and the mixture was stirred at 17° C. for 16 hr. The reaction mixture was diluted with water and ethyl acetate, and saturated aqueous sodium bicarbonate was added thereto. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.65 g).

Workup

  1. temperaturecooling
  2. additionwas added
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d1e855cd929b4e5a868c5be7091b62b2
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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