Oxalyl chloride → Benzoic acid, 2-chloro-6-nitro-, methyl ester

HRID 598086Notes

Reaction equation

HRID 598086 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:14](Cl)(=O)C(Cl)=O>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 792872-Chloro-6-nitrobenzoic acid

Product 1

HCID 603613Benzoic acid, 2-chloro-6-nitro-, methyl esterYield 95.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension containing 3.0 g (15 mmol) of 2-chloro-6-nitrobenzoic acid in 150 ml of dichloromethane was added 2.8 g (22 mmol) of oxalyl chloride followed by 0.055 ml (0.75 mmol) of N,N-dimethylformamide. The reaction was allowed to stir at room temperature for 2 h, quenched with 50 ml of methanol and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 10% ethyl acetate/hexanes gave 3.1 g (9-7%) of product.

Workup

  1. customquenched with 50 ml of methanol
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationFiltration, removal of solvent and purification of the residue via biotage
  7. washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2037e4060daa427994f5bba795226983
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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