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

HRID 385082Notes

Reaction equation

HRID 385082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F: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]([F:13])[C:10]=1[O:11][CH3:12])[C:5]([Cl:23])=[O:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 38625473-Chloro-5-fluoro-4-methoxybenzoic acid

Product 1

HCID 37390793-Chloro-5-fluoro-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-chloro-5-fluoro-4-methoxybenzoic acid (295 mg), toluene (3 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.15 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 used for the synthesis of (b).

Workup

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

Sources & evidence

ORD record
ord-6dc2a5260df94ceea39ec2486633e060
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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