1,4-Dibromobenzene → HCID 69199606, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (0.250 g, 1.00 mmol), 1,4-dibromo benzene (0.259 g, 1.10 mmol), Pd(PPh3)4 (0.0580 g, 5%), and CsF (0.456 g, 3.00 mmol) in DME/MeOH (25 mL, 1:1) was heated at 70° C. overnight. The reaction mixture was concentrated and the residue was extracted with CH2Cl2, washed with water, dried over MgSO4, filtered, concentrated, and purified by flash chromatography eluted with hexane/CH2Cl2 (1:9) to give 0.151 g (54%) of the desired product. MS (DCI/NH3) m/z: 279.9 (M+H)+; 1H NMR (300 MHz, CD3OD) δ 3.91 (s, 3H), 6.86 (d, J=8.14 Hz, 1H), 7.06 (m, 1H), 7.14 (d, J=2.03 Hz, 1H), 7.44-7.58 (m, 3H).

Provenance & Evidence