Cesium carbonate → 2'-Methyl-4'-nitro-biphenyl-3-sulfinic acid methyl ester

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Reaction Steps

A solution of 3-bromobenzene methyl sulfinate (541 mg, 2.3 mmol), 4,4,5,5-tetramethyl-2-(2-methyl-4-nitro-phenyl)-[1,3,2]dioxaborolane (484 mg, 1.84 mmol), cesium carbonate (900 mg, 2.76 mmol), and Pd(dppf)Cl2 (145 mg, 0.18 mmol) was stirred in DMF at 80° C. for 4 h under argon. The mixture was partitioned between EtOAc (100 mL) and aq NH4Cl (30 mL) and the layers were separated. The organic layer was further washed with water (4×30 mL), brine (30 mL), and was dried over Na2SO4. Concentration of the solution followed by purification of the residue via silica gel chromatography (2-10% EtOAc in hexanes) yielded the product as a colorless oil (300 mg, 56%). 1H NMR (CDCl3): δ 8.19 (m, 1H), 8.12 (ddd, 1H, J=0.6, 2.5, 8.4 Hz), 7.77 (ddd, 1H, J=1.2, 1.8, 7.8 Hz), 7.65-7.71 (m, 2H), 7.54 (ddd, 1H, J=1.2, 1.8, 7.6 Hz), 7.41 (d, 1H, J=8.4 Hz), 6.65 (s, 1H), 3.58 (s, 3H), 2.38 (s, 3H).

Provenance & Evidence