Tetrahydrofuran → HCID 21906932, compound

Participants

Reaction Steps

5-Benzyloxyindole (500 mg, 2.24 mmol) was dissolved in THF (20 mL) and treated with 1M KOtBu in THF (2.24 mL, 2.24 mmol). After stirring for 3 hours, 3-fluorobenzyl bromide (274 μL, 2.24 mmol) was added and the reaction mixture was stirred for an additional 24 hrs. Standard aqueous workup and purification by silica gel chromatography, eluting with 5:1 hexanes/ethyl acetate, provided N-(2-fluorobenzyl)-5-benzyloxyindole (325 mg, 44%). 1H NMR (200 MHz, CDCl3) δ 7.55–7.29 (mn, 5H), 7.28–7.05 (m, 3H), 7.04–6.81 (m, 5H), 6.49 (dd, J=0.7, 3.1 Hz, 1H), 5.26 (s, 2H), 5.10 (s, 2H). MS (EI, m/z) M+=33 1.

Provenance & Evidence