Dichloromethane → Dimethyl 2,3-biphenyldicarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl 3-iodophthalate (WO 2008/115516) (1.00 g, 3.12 mmol), phenylboronic acid (0.571 g, 4.69 mmol), K2CO3 (0.880 g, 9.30 mmol) in 1,4-dioxane (15 mL) and water (4 mL) was purged with nitrogen for 30 min. Pd(dppf)Cl2:DCM (0.219 g, 0.312 mmol) was added and the reaction mixture was heated at 100° C. for 12 h. The reaction mixture was filtered through a pad of CELITE® and the pad was washed with water (50 mL). The filtrate was extracted with EtOAc (2×100 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by combiflash (REDISEP®, silica gel, 12 g, 20% EtOAc/hexanes) to obtain dimethyl [1,1′-biphenyl]-2,3-dicarboxylate (0.65 g, 77.0%) as an off-white solid. LCMS (Condition 11): retention time 0.96 min, [M-MeOH+1]=239.3. 1H NMR (400 MHz, DMSO-d6) δ 3.59 (s, 3 H), 3.85 (s, 3 H), 7.33-7.49 (m, 5 H), 7.68-7.70 (m, 2 H), 7.95-8.00 (m, 1 H).

Provenance & Evidence