Methyl iodide → 2-Fluoro-4-methoxyaniline

3-Fluoro-4-nitrophenol (10.17 g, 64.7 mmol) (Aldrich) was dissolved in dimethylformamide (210 mL). Potassium carbonate (45 g, 323 mmol) and methyl iodide (5 mL, 77.64 mmol) (Aldrich) were added and the reaction mixture was stirred at room temperature overnight. (TLC: 20% ethyl acetate in hexanes showed complete conversion). The reaction mixture was filtered through a bed of Celite®, and concentrated under reduced pressure. The crude material was triturated with ether and insoluble materials were removed by filtration. The filtrate was concentrated under reduce pressure to afford an orange solid. This material (11.43 g) was dissolved in methanol (150 mL) and hydrogenated for 1.5 hours in a Parr apparatus at 50 psi, in the presence of 10% palladium on carbon (1.5 g) (Aldrich). (TLC: 20% ethyl acetate in hexanes showed complete conversion). The reaction mixture was filtered through Celite® washed with ethyl acetate, then concentrated under reduced pressure to afford 2-fluoro-4-methoxyaniline as a solid. (Yield 3.81 g, 26.99 mmol).

1. filtrationThe reaction mixture was filtered through a bed of Celite®
2. concentrationconcentrated under reduced pressure
3. customThe crude material was triturated with ether and insoluble materials
4. customwere removed by filtration
5. concentrationThe filtrate was concentrated
6. customto afford an orange solid
7. filtrationThe reaction mixture was filtered through Celite®
8. washwashed with ethyl acetate
9. concentrationconcentrated under reduced pressure

ORD record

ord-b4f910558399475e9c20301f6158168a

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115740B2