2-Fluoro-4-iodoaniline → HCID 67083703, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluoro-4-iodo-aniline (2.24 g, 9.43 mmol) in anhydrous THF (30 ml) under an atmosphere of nitrogen was added 1M LHMDS in hexanes (18 ml, 1M, 18.0 mmol) keeping the internal temperature below −65° C. After complete addition the reaction mixture was stirred for 30 minutes at −70° C. A solution of 2-dimethoxymethyl-1,3-difluoro-4-nitro-benzene (2.0 g, 8.58 mmol) in anhydrous THF (20 ml) was added to the reaction mixture keeping the internal temperature below −68° C. After complete addition the reaction mixture was stirred for 30 minutes at −70° C. then allowed to warm to room temperature and stirred for 22 hours. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with ethyl acetate (200 ml). The organic layer was washed with brine, dried (Na2SO4), concentrated in vacuo to a minimum volume and triturated with cyclohexane to yield the title compound (2.18 g, 56%). LCMS (Method B): RT=4.26 min, [M−H]−=449.

Provenance & Evidence