Sodium Chloride → 4'-Methyl-2-nitro-1,1'-biphenyl

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Reaction Conditions

Reaction Steps

Under N2, a clean, dry flask was charged with p-tolyltrimethyltin (from Example 12, Step B) (5.61 g, 0.022 mol), 2-bromonitrobenzene (4.04 g, 0.020 mol), anhydrous DMF (40 mL), and palladium(II) bis(triphenylphosphine)dichloride (140 mg, 0.2 mmol), heated at 110° C. and stirred for 4 h when TLC (4:1 hexane/EtOAc) indicated disappearance of starting materials. The nearly black reaction mixture was cooled to room temperature, poured into a solution made from 100 mL 1N KOH and 100 mL sat. NaCl, and extracted with 3×150 mL EtOAc. The combined, organic layers were washed with 100 mL 1N KOH and 100 mL sat. NaCl, and then dried over anhydrous Na2SO4. After filtration, the amber solution was evaporated to dryness and then flash chromatographed over 900 mL SiO2, eluting with 2.5% EtOAc-hexane to give 4.109 g (96%) of the title compound as a light orange liquid, homogeneous on TLC (4/1 hex-EtOAc).

Provenance & Evidence