4-Bromotoluene → HCID 10420469, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried resealable Schlenk tube was charged with CuI (190 mg, 0.998 mmol), K3PO4 (2.10 g, 9.89 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (0.60 mL, 5.00 mmol), 4-bromotoluene (0.70 mL, 5.69 mmol) and dioxane (3.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 70 h. The resulting dark brown suspension was cooled to room temperature and filtered through a 2×1 cm pad of Celite eluting with 50 mL of dichloromethane. The black filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; dichloromethane saturated with aq NH3-methanol 50:1; 15 mL fractions). Fractions 9-11 provided 650 mg (64% yield) of the product as a brown solid. 1H NMR (400 MHz, CDCl3): δ 7.00-6.95 (m, 2H), 6.62-6.57 (m, 2H), 3.30 (br s, 1H), 2.96-2.86 (br m, 1H), 2.49 (td, J=10.4, 3.6, 1H), 2.23 (s, 3H), 2.17-2.08 (m, 1H), 2.02-1.94 (m, 1H), 1.79-1.66 (m, 2H), 1.44 (br s, 2H), 1.38-1.17 (m, 3H), 1.07-0.95 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 145.9, 129.7, 126.6, 113.9, 60.5, 56.1, 35.2, 32.4, 25.3, 25.0, 20.3.

Provenance & Evidence