Thionyl Chloride → 5-(Chloromethyl)-2-methoxybenzonitrile

HRID 1167322Notes

Reaction equation

HRID 1167322 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9].S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:15][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 229961945-(Hydroxymethyl)-2-methoxybenzonitrile

Product 1

HCID 229961915-(Chloromethyl)-2-methoxybenzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-hydroxymethyl-2-methoxy-benzonitrile (500 mg, 3.064 mmol) in toluene (10 mL) cooled to 0° C. was added thionyl chloride (338 μL, 4.596 mmol). The reaction mixture was heated at reflux for 3 h. The reaction mixture was concentrated in vacuo to afford 5-chloromethyl-2-methoxy-benzonitrile as a white solid (500 mg, 90%). The product was used without firther purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ee3df3823321431aa909ebae7f3c3870
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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