Dimethylformamide → 4-Chlorocarbonyl-3-fluoro-benzoic acid methyl ester

HRID 589507Notes

Reaction equation

HRID 589507 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[C:6]([F:13])[CH:5]=1.C(Cl)(=O)C([Cl:18])=O.CN(C=O)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([Cl:18])=[O:9])=[C:6]([F:13])[CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 592950932-Fluoro-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 867310014-Chlorocarbonyl-3-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-terephthalic acid 4-methyl ester (J. Med. Chem., 52(19), 5950-5966; 2009) (500 mg, 2.25 mmol) was suspended in DCM (10 ml). Then oxalyl chloride (5.08 ml, 58.0 mmol) and a drop of DMF were added. The resulting mixture was refluxed for 14 hrs. The solvents were removed in vacuo, and the resulting crude Intermediate 33 was used in the next step without purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 14 hrs
  2. customThe solvents were removed in vacuo
  3. customthe resulting crude Intermediate 33 was used in the next step without purification

Sources & evidence

ORD record
ord-96fa0fbf51974fbc95273a4c266cfbfe
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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