4-Fluoroaniline → HCID 11710337, compound

Participants

Reaction Steps

A mixture of N-[4-cyano-3-(trifluoromethyl)phenyl]-N-ethyl glycine, Example 91B (0.074 g, 0.25 mmol), and resin bounded carbodiimide (0.50 g, 1.26 mmol/g) was shaken in CH2Cl2 (15 mL) for 30 min, then 4-fluoroaniline (0.044 g, 0.4 mmol) was added, and the mixture was shaken for another 12 h. The resin was filtered and washed with CH2Cl2 (2×10 mL). The resulting filtrate was concentrated under vacuum. The residue was triturated with Et2O to obtain 0.018 g (11%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.42-7.39 (m, 2H), 7.06-6.99 (m, 4H), 6.85 (dd, J=9.0, 2.7 Hz, 1H), 4.10 (s, 2H), 3.64 (q, J=7.1 Hz, 2H), 1.31 (t, J=7.1 Hz, 3H); MS (APCI) m/z 366 (M+1).

Provenance & Evidence