Sodium Chloride → 5-(4-fluorophenyl)-1H-indole

Participants

Reaction Steps

Combine 5-bromoindole (5.00 g, 25.50 mmol) and Pd(Ph3P)4 (1.47 g, 1.28 mmol) in toluene (510 ml). After 30 minutes, add a solution of 4-fluorobenzeneboronic acid (5.35 g, 38.26 mmol) in ethanol (153 ml) then add saturated NaHCO3 (255 ml). Heat to reflux. After 4 hours, cool to ambient temperature, pour into saturated NaCl (250 ml), and separate the organic layer. Extract the aqueous layer with ethyl acetate. Combine the organic extracts, wash with brine, dried, then evaporate to residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexanes (10/90) to give the title compound: mp 84–89° C. MS (ACPI): m/e 212.0 (M+1). Analysis for C14H10FN: Calcd: C, 79.60; H, 4.77; N, 6.63; found: C, 79.33; H, 4.92; N, 6.64.

Provenance & Evidence