Hydrofluoric Acid → 4-Fluoro-3-methoxyaniline

A solution of 10.73g. (0.07 mole) of 3-methoxyphenylazide in 100 ml. of hexane was added to 20 ml. of concentrated hydrofluoric acid and the reaction mixture, contained in a bomb, was aged for 10 hours at room temperature with agitation. The reaction mixture was then cooled, vented, and poured from the bomb. The bomb was then rinsed with 50 ml. of water, followed by 20 ml. of dichloromethane. The reaction mixture poured from the bomb was blown down under nitrogen, and then combined with the bomb rinsings, and this mixture was cooled and brought to a pH of about 12 with KOH pellets. The mixture was extracted three times with 50 ml. of dichloromethane per extraction, and the combined extracts were dried over MgSO4 and concentrated to 7.31g. (53%) of a dark oil. An aliquot of this product was distilled under reduced pressure to obtain a pale yellow oil with a b.p. of 150°-152° C. at 50 mm. Hg. Structure of the final product as 3-methoxy-4-fluoroaniline was confirmed by mass spectroscopy.

1. temperatureThe reaction mixture was then cooled
2. additionpoured from the bomb
3. washThe bomb was then rinsed with 50 ml
4. additionThe reaction mixture poured from the bomb
5. temperaturethis mixture was cooled
6. extractionThe mixture was extracted three times with 50 ml
7. extractionof dichloromethane per extraction
8. dry with materialthe combined extracts were dried over MgSO4
9. concentrationconcentrated to 7.31g
10. distillationAn aliquot of this product was distilled under reduced pressure
11. customto obtain a pale yellow oil with a b.p. of 150°-152° C. at 50 mm. Hg

ORD record

ord-711f4c76fd794b3a97bab1f5cb8882a5

Source dataset

uspto-grants-1979_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04145364