ChemicalBook CAS DataBase List 3-Fluoro-4-nitrobenzoic acid

3-Fluoro-4-nitrobenzoic acid synthesis

5synthesis methods

Product Name:3-Fluoro-4-nitrobenzoic acid
CAS Number:403-21-4
Molecular formula:C7H4FNO4
Molecular Weight:185.11

To a solution of 3-fluoro-4-nitrobenzyl alcohol (2.97 g) in acetone (60 ml) was added Jones reagent (13 ml), prepared from chromic acid (26.7 g) and sulfuric acid (23 ml) in water (100 ml), dropwise at 0°C. The mixture was stirred on a ice-bath for 0.5 h and quenched with isopropanol (20 ml) to be concentrated in vacuo. The residue was dissolved in ethyl acetate (30 ml) and washed with water (30 ml X 3), and brine (30 ml X 1), successively. The organic layer was dried over sodium sulfate and concentrated in vacuo to obtain a yellow solid, that was triturated with hexane. 3-fluoro-4-nitrobenzoic acid as a pale yellow solid (2.94 g, 92%).
3-Fluoro-4-nitrobenzoic acid synthesis

446-34-4
298 suppliers
$7.00/5g

403-21-4
252 suppliers
$6.00/1g

Yield:403-21-4 83%

Reaction Conditions:

with potassium dichromate;sulfuric acid in acetic acid at 120; for 2 h;

Steps:

445
2-Fluoro-4-methyl-l-nitro-benzene (1.0 g, 12.9 mmol) was added portion- wise to a suspension of potassium dichromate (5.04 g, 17.16 mmol) in glacial acetic acid (8 mL) follow by concentrated sulfuric acid (3.6 mL). The reaction mixture was heated to 120⁰C for 2 h and then allowed to cool to ambient temperature. The reaction was quenched with crushed ice and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-fluoro-4-nitro-benzoic acid (1.9 g, 83%) as a white solid.

References:

F2G LTD WO2009/130481, 2009, A1 Location in patent:Page/Page column 145

FullText

503315-74-0 Synthesis