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

HRID 391242Notes

Reaction equation

HRID 391242 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) obtained in Step IV was suspended in toluene (50 ml), and thionyl chloride (4.56 g) was added dropwise at 65-75° C. After the dropwise addition, the mixture was stirred for 1 hr and concentrated under reduced pressure. Toluene (30 ml) was added to the residue, and the mixture was concentrated again under reduced pressure. The residue was dissolved in toluene (30 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. additionAfter the dropwise addition
  2. concentrationconcentrated under reduced pressure
  3. additionToluene (30 ml) was added to the residue
  4. concentrationthe mixture was concentrated again under reduced pressure
  5. dissolutionThe residue was dissolved in toluene (30 ml)

Sources & evidence

ORD record
ord-faf587d1507246bcb0c6f083e3a6c83d
Source dataset
uspto-grants-2013_02
Patent number
US08383819B2

Reaction notes

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