Sodium Carbonate → 2-Nitrobiphenyl

Participants

Reaction Steps

Aqueous sodium carbonate (2 M, 100 mL), followed by tetrakis(triphenylphosphine) palladium (340. mg, 0.297 mmol), were added to a solution of 2-bromonitrobenzene (2.00 g, 9.90 mmol) and phenylboronic acid (1.27 g, 9.90 mmol) in dimethoxyethane (125 mL). The reaction mixture was heated to reflux for 3 hours. The reaction crude was then cooled to room temperature, diluted with water (100 mL) and the product extracted with CH2Cl2 (4×50 mL). The organic phase was dried over MgSO4, and concentrated under reduced pressure to yield a yellow solid, which was further purified via flash chromatography over silica, eluting with a gradient of hexanes to 20% CHCl3/80% hexanes. The nitro 2 was obtained as a yellow oil that was further dried under high vacuum for 24 h (1.79 g, 90.1%).

Provenance & Evidence