Dimethylformamide → Methyl 2,3-difluoro-5-nitrobenzoate

HRID 2171224Notes

Reaction equation

HRID 2171224 reaction equation
C(Cl)(=O)C(Cl)=O.CN([CH:10]=[O:11])C.C(Cl)Cl.[F:15][C:16]1[C:24]([F:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[CH:21][C:17]=1[C:18](O)=[O:19]>CO>[F:15][C:16]1[C:24]([F:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[CH:21][C:17]=1[C:18]([O:11][CH3:10])=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 545937902,3-Difluoro-5-nitrobenzoic acid

Product 1

HCID 62662214Methyl 2,3-difluoro-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Oxalyl chloride (1 ml) and DMF (5 μl) were added to a CH2Cl2 (1.6 ml) solution containing 2,3-difluoro-5-nitrobenzoic acid (1.61 g) obtained in the 1st step, followed by stirring at room temperature for 15 minutes. The reaction solution was poured into a liquid mixture of MeOH/Py (100 ml/1.28 ml) and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1). A light yellow solid of methyl 2,3-difluoro-5-nitrobenzoate (1.71 g) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. distillationthe solvent was distilled away under reduced pressure
  3. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 4:1)

Sources & evidence

ORD record
ord-e96574f100e948fc8f2c384cb915ea24
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

Loading…