Aniline → N-(2-fluoroethyl)aniline

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask aniline (0.5 g, 5.4 mmol), 2,6-lutidine (0.58 g, 5.4 mmol) and 2-fluoroethyl tosylate (12; prepared according to Example 2(a)) (1.17 g, 5.4 mmol) were combined in DMF (2.5 mL) and stirred at 100° C. overnight. The reaction was allowed to cool and then diluted with ethyl acetate (50 mL). This was washed with water (3×20 mL) and the organics were dried and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (100 g, 0-100% B, 18 CV, 85 mL/min) to give 435 mg (60%) of (2-fluoro-ethyl)-phenyl-amine (24) as a yellow oil. The structure was confirmed by 1H NMR (300 MHz, CDCl3) δH 3.41 (1H, t, J=3 Hz, NCH2CH2F), 3.50 (1H, t, J=3 Hz, NCH2CH2F), 3.93 (1H, s, br), 4.54 (1H, t, J=3 Hz, NCH2CH2F), 4.71 (1H, t, J=3 Hz, NCH2CH2F), 6.65-6.82 (3H, m, 2×NCCH, NCCHCHCH), 7.14-7.28 (2H, m, 2×NCCHCHCH).

Provenance & Evidence