ChemicalBook CAS DataBase List methyl 2-fluoro-3-nitrobenzoate

methyl 2-fluoro-3-nitrobenzoate synthesis

9synthesis methods

Product Name:methyl 2-fluoro-3-nitrobenzoate
CAS Number:946126-94-9
Molecular formula:C8H6FNO4
Molecular Weight:199.14

A solution of 2-fluoro-3-nitrobenzoic acid (5 g, 27.0 mmol) in MeOH (50 mL) was treated with concentrated H2SO4 (1.4 mL, 27.0 mmol) and the resulting reaction was stirred at 50 °C for 16 h. The solvent was removed under reduced pressure and the residue was diluted with EtO Ac. The organic solution was washed with saturated aqueous NaHCO3 solution until the water phase reached neutral pH. The two phases were separated. Organics were washed with water, brine and dried (Na2SO4). The solution was filtered and concentrated to give crude methyl 2-fluoro-3-nitrobenzoate which was used as is in the next step. (5.1 g, 25.2 mmol, 93 %) as a pale yellow solid.

67-56-1 Synthesis

67-56-1
752 suppliers
$9.00/25ml

317-46-4 Synthesis

317-46-4
292 suppliers
$6.00/1g

946126-94-9
158 suppliers
$28.00/1g

Yield:946126-94-9 99%

Reaction Conditions:

Stage #1: 2-fluoro-3-nitro-benzoic acidwith oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 20;
Stage #2: methanol in dichloromethane; for 0.0833333 h;

Steps:

General procedure 3: Ester synthesis:

General procedure: To a suspension/solution of carboxylic acid (1.0 eq.) in dry DCM (0.5 M) was added oxalyl chloride (1.1 eq.) and DMF (0.05 eq.) and the mixture was stirred at room temperature until complete gas evolution. Excess MeOH was added and after 5 minutes the solvent was removed under reduced pressure and the product dried in vacuo and used without further purification.

References:

Kl?vekorn, Philip;Pfaffenrot, Bent;Juchum, Michael;Selig, Roland;Albrecht, Wolfgang;Zender, Lars;Laufer, Stefan A. [European Journal of Medicinal Chemistry,2021,vol. 210] Location in patent:supporting information

3970-35-2 Synthesis