Thionyl Chloride → Methyl 3-(chlorocarbonyl)benzoate

HRID 1018323Notes

Reaction equation

HRID 1018323 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7](O)=[O:8])[CH:5]=1.S(Cl)([Cl:16])=O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([Cl:16])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 15563901Methyl 3-(chlorocarbonyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isophthalic acid mono methyl ester (200 mg, 1.10 mmol) was heated at reflux for 15 min in the mixture of thionyl chloride (2 ml) and DMF (cat.). The solvent was evaporated in vacuo, the residue was dissolved in DCM (5mi) and the solvent was evaporated to afford 3-chlorocarbonyl-benzoic acid methyl ester. To a solution of the product of step b above (435 mg, 1.00 mmol) and triethylamine (280 μl, 2.00 mmol) in DCM (10 ml) was added a solution of the previously prepared 3-chlorocarbonyl-benzoic acid methyl ester in DCM (2 ml). The reaction mixture was stirred at room temperature for 1h. It was washed with 5% aqueous potassium hydrogen sulfate (10 ml) and water (10 ml), dried (MgSO4) and the solvent was evaporated. The residue was purified by flash column chromatography (silica, DCM/ethyl acetate 4:1) to afford the product as a white solid (310mg, 52%). 1H NMR (300 MHz, CDCl3) 8.53 (1H, s), 8.18 (2H, m), 8.07 (1H, d), 7.51 (1H, t), 7.30-7.21 (4H, m), 3.95 (3H, s), 2.91 (2H, m), 2.20 (3H, s), 1.94 (3H, br s), 1.66 (6H, m), 1.5 (6H, s), 1.38 (2H, m), 1.21 (9H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in DCM (5mi)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f28698873fc84c9bbf907aa4216c77df
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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