Boron trifluoride etherate → HCID 90253497, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of C85 (2.58 g, 14.2 mmol) in toluene (50 mL) cooled to −78° C. was added boron trifluoride diethyl etherate (4.23 mL, 15.9 mmol) drop-wise. After stirring for 30 minutes at −78° C., 2,4-difluoro-1-iodobenzene (3.90 g, 15.9 mmol) was added, followed by drop-wise addition of n-butyllithium (2.5 M in hexanes, 6.04 mL, 15.1 mmol). The reaction was stirred at −78° C. for 90 minutes at which point saturated aqueous ammonium chloride solution (10 mL) was added. The reaction was allowed to warm to room temperature and then taken up in ethyl acetate. The organic layer was washed with water and with saturated aqueous sodium chloride solution and then concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 25% ethyl acetate in heptane) provided the product as a colorless oil. Yield: 1.25 g, 4.23 mmol, 30%. LCMS m/z 296.2 [M+H+]. 1H NMR (400 MHz, CDCl3): characteristic peaks δ 7.82-7.88 (m, 1H), 6.79-6.84 (m, 1H), 6.68-6.74 (m, 1H), 3.93-3.97 (m, 1H), 3.72-3.76 (m, 1H), 3.63-3.66 (m, 1H), 3.44-3.48 (m, 1H), 2.83-2.98 (m, 1H), 1.83-1.92 (m, 1H), 1.44-1.59 (m, 1H), 0.99-1.01 (m, 1H), 0.72-0.87 (m, 1H).

Provenance & Evidence