Toluene → 3-Chloro-5-cyano-4-methoxybenzoyl chloride

HRID 385025Notes

Reaction equation

HRID 385025 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:13]#[N:14])[C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].C1(C)C=CC=CC=1.S(Cl)([Cl:24])=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:13]#[N:14])[C:10]=1[O:11][CH3:12])[C:5]([Cl:24])=[O:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 33779600HCID 33779600, compound

Product 1

HCID 866681513-Chloro-5-cyano-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-chloro-5-cyano-4-methoxybenzoic acid (932 mg), toluene (9.3 mL), N,N-dimethylformamide (0.03 mL) and thionyl chloride (0.38 mL) were added, and the mixture was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene to obtain the title compound (993 mg) as a brown solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-61bffe82ad7f42468e8481776676bb3a
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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