Iodoethane → Ethyl 2-fluoro-4-nitrobenzoate

To a dry 100 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet were added 3.00 g of 2-fluoro-4-nitrobenzoic acid, 3.00 g of NaHCO3, and 20 mL of anhydrous dimethylacetamide. The suspension was treated with 3.50 mL of ethyl iodide and stirred at RT under N2 for 18 h. The reaction mixture was filtered to remove solids and the filtrate concentrated in vacuo to give an orange residue which was dissolved in 100 mL of CH2Cl2. The solution was washed with saturated aqueous NaHCO3 (3×50 mL), water (1×60 mL), and dried over anhydrous Na2SO4. Removal of drying agent by filtration and passage through a silica gel plus (3×5 cm) gave a light yellow solution which was concentrated in vacuo to afford 3.10 g (90%) of ethyl 2-fluoro-4-nitrobenzoate as a light yellow crystalline solid, m.p. 70-73° C.

1. customTo a dry 100 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet
2. filtrationThe reaction mixture was filtered
3. customto remove solids
4. concentrationthe filtrate concentrated in vacuo
5. customto give an orange residue which
6. washThe solution was washed with saturated aqueous NaHCO3 (3×50 mL), water (1×60 mL)
7. dry with materialdried over anhydrous Na2SO4
8. customRemoval
9. customof drying agent
10. filtrationby filtration and passage through a silica gel plus (3×5 cm)
11. customgave a light yellow solution which
12. concentrationwas concentrated in vacuo

ORD record

ord-82567e7d5c44455592175266a6bae8be

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06140100