ChemicalBook CAS DataBase List Methyl 5-fluoro-2-methyl-3-nitrobenzoate

Methyl 5-fluoro-2-methyl-3-nitrobenzoate synthesis

9synthesis methods

Product Name:Methyl 5-fluoro-2-methyl-3-nitrobenzoate
CAS Number:697739-03-0
Molecular formula:C9H8FNO4
Molecular Weight:213.16

Methyl 5-fluoro-2-methyl-3-nitrobenzoate synthesis: To a solution of conc. H2SO4 (700mL) was added portionwise 5-fluoro-2-methylbenzoic acid (80g, 520 mmol) at -5-0°C. Then a mixture of conc. HNO3(60.4 g. 624 mmol) in conc. H2SO4 (60 mL) was added drop-wise at -5-0°C. in a period of about 1.5 hrs. After the addition, the mixture was stirred at this temperature for 2 hrs. TLC (petroleum ether/ EtOAc=1:1) showed the reaction was complete. The mixture was poured into crash ice with vigorous stirring and the precipitate was collected by filtration. The precipitate was dissolved in EtOAc, washed with brine, dried over anhydrous Na2SO4 concentrated to give crude 5-fluoro-2-methyl-3-nitrobenzoic acid (54 g). A solution of this crude 5-fluoro-2-methyl-3-nitrobenzoic acid (54 g) in dry methanol (500 mL) was cooled to 0°C., SOCl2 (64.52g, 542.3 mmol) was added drop-wise. After the addition, the mixture was heated to reflux for 16hrs. TLC (petroleum ether/EtOAc=1:1) showed the reaction was complete. Solvent was removed under reduced pressure to give crude product. The crude product was purified by silica gel chromatography (petroleum ether to petro leum ether/EtOAc=50: 1) to give methyl 5-fluoro-2-methyl-3-nitrobenzoate (28 g, yield 25% for two steps) as a white solid.

67-56-1 Synthesis

67-56-1
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850462-64-5 Synthesis

850462-64-5
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$11.00/250mg

Methyl 5-fluoro-2-methyl-3-nitrobenzoate

697739-03-0
165 suppliers
$8.00/250mg

Yield:697739-03-0 96%

Reaction Conditions:

with thionyl chloride for 3 h;Cooling with ice;Reflux;

Steps:

2.212.1 Step 1

Dissolve 5-fluoro-2-methyl-3-nitrobenzoic acid in 20ml of methanol, add dichlorosulfoxide (728ul, 10.04mmol) under ice bath, warm to reflux for 3h, after the reaction is complete, Spin dry, dilute with ethyl acetate, wash with saturated sodium bicarbonate and saturated sodium chloride respectively, and dry to obtain the target product 1.025g, yield 96%.

References:

CN110963994,2020,A Location in patent:Paragraph 0475; 1148-1150

850462-64-5 Synthesis

850462-64-5
96 suppliers
$11.00/250mg