Toluene → 3,5-Dichloro-4-methoxybenzoyl chloride

HRID 385004Notes

Reaction equation

HRID 385004 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:13])[C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].C1(C)C=CC=CC=1.S(Cl)([Cl:23])=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:13])[C:10]=1[O:11][CH3:12])[C:5]([Cl:23])=[O:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 721135Benzoic acid, 3,5-dichloro-4-methoxy-

Product 1

HCID 38303153,5-Dichloro-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3,5-dichloro-4-methoxybenzoic acid (8.81 g), toluene (170 mL), N,N-dimethylformamide (5 droplets) and thionyl chloride (6.0 mL) were added, and then the mixture was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure and the obtained residue was azeotroped with toluene and then used for the synthesis of (c).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe obtained residue was azeotroped with toluene
  3. customused for the synthesis of (c)

Sources & evidence

ORD record
ord-cab27125e60342dc9e9fc0a0a8f997f1
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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