3-(difluoromethoxy)-2-fluoroaniline

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-difluoromethoxy-2-fluoro-3-nitro-benzene (2.16 g, 10.43 mmol) and tin(II) chloride (6.92 g, 36.5 mmol) in 2-propanol (100 ml) was added carefully HCl (37%, 10.28 ml, 125 mmol) and the mixture was stirred for 30 min at 110° C. The reaction mixture was cooled to RT, diluted with water and the pH adjusted to 10 by addition of 2N NaOH. The mixture was extracted with EtOAc and the organic layer was dried over Na2SO4, filtered and concentrated to afford the titled compound. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.06 (t, 1H), 6.95 (m, 1H), 6.87 (m, 1H), 6.55 (td, 1H), 5.04 (bs, 2H). tR (HPLC conditions f): 1.93 min. The reaction mixture was cooled to RT The mixture was extracted with EtOAc the organic layer was dried over Na2SO4 filtered concentrated