Thionyl Chloride → 1-[4-(chloromethyl)phenyl]-1H-pyrazole

HRID 629360

Reaction equation

HRID 629360 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.S(Cl)([Cl:16])=O>ClCCCl>[Cl:16][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2776480(4-(1H-Pyrazol-1-yl)phenyl)methanol

Product 1

HCID 71308871-[4-(chloromethyl)phenyl]-1H-pyrazoleYield 88.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [4-(1H-pyrazol-1-yl)phenyl]methanol (24.0 g) in 1,2-dichloroethane (200 mL) was added dropwise thionyl chloride (26.3 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with tert-butyl methyl ether to give the title compound (23.5 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washthe residue was washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-ea17e41ecbc64cc78503693b80ae55f2
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Linked notes

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