Thionyl Chloride → 5-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl chloride

HRID 391247Notes

Reaction equation

HRID 391247 reaction equation
[Cl:1][C:2]1[C:3]([F:21])=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][C:6]1[C:7]([O:16][CH3:17])=[CH:8][C:9]([F:15])=[C:10]([CH:14]=1)[C:11](O)=[O:12].S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([F:21])=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][C:6]1[C:7]([O:16][CH3:17])=[CH:8][C:9]([F:15])=[C:10]([CH:14]=1)[C:11]([Cl:24])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 575728415-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoic acid

Product 1

HCID 575728405-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoic acid (10 g) was suspended in toluene (50 ml) with stirring at room temperature, thionyl chloride (4.57 g) was added dropwise at 65-75° C., and the mixture was stirred for 1.5 hr. After cooling, the solvent was concentrated under reduced pressure, toluene (50 ml) was added to the residue, and the mixture was concentrated again under reduced pressure. The residue was dissolved in toluene (20 ml) to give a solution of 5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl chloride in toluene. This was identified as the title compound by HPLC.

Workup

  1. stirringthe mixture was stirred for 1.5 hr
  2. temperatureAfter cooling
  3. concentrationthe solvent was concentrated under reduced pressure, toluene (50 ml)
  4. additionwas added to the residue
  5. concentrationthe mixture was concentrated again under reduced pressure
  6. dissolutionThe residue was dissolved in toluene (20 ml)

Sources & evidence

ORD record
ord-3e78f13e69d34d57ad6ca2a1f6b19f81
Source dataset
uspto-grants-2013_02
Patent number
US08383819B2

Reaction notes

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