Water → (4-Fluoro-2-iodophenyl)methanamine

Temperature

55 °C

A solution of 1-(azidomethyl)-4-fluoro-2-iodobenzene (15.2 g, 54.8 mmol) in DMF (35 ml) at 0° C. was treated with triphenylphosphine (21.6 g, 81.2 mmol) and then stirred for 1 h. The reaction mixture was then treated with water (5 ml) and heated at 55° C. for 1 h. The DMF was concentrated in vacuo and the residue was diluted with ethyl acetate (200 ml). The organic phase was extracted with 0.5 N hydrochloric acid (140 ml) and the aqueous extract was washed with ethyl acetate. The aqueous phase was then adjusted to pH 9 with 1 N LiOH and extracted with ethyl acetate (2×200 ml). The combined organic phases were dried over anhydrous magnesium sulfate and concentrated. The residue was diluted with ether (200 ml), filtered and concentrated. Distillation of the residue in vacuo gave 8.52 g (62% yield) of the title amine as a clear oil: bp 85° C./0.35 torr (bulb to bulb distillation air bath temperature). 1HNMR 400 MHz (DMSO-d6) δ (ppm): 3.64 (2H, s, CH2), 7.27 (1H, m, aromatic), 7.53 (1H, dd, J=6 Hz and J=8.6H, aromatic), 7.83 (1H, dd, J=3 Hz and J=8 Hz, aromatic).

1. concentrationThe DMF was concentrated in vacuo
2. additionthe residue was diluted with ethyl acetate (200 ml)
3. extractionThe organic phase was extracted with 0.5 N hydrochloric acid (140 ml)
4. extractionthe aqueous extract
5. washwas washed with ethyl acetate
6. extractionextracted with ethyl acetate (2×200 ml)
7. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
8. concentrationconcentrated
9. additionThe residue was diluted with ether (200 ml)
10. filtrationfiltered
11. concentrationconcentrated
12. distillationDistillation of the residue in vacuo

ORD record

ord-b327ee11ada24987a7e3041aa2212885

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491819B1