Sodium Carbonate → Biphenyl

Participants

Reaction Conditions

Reaction Steps

In 10 ml of toluene was added 600 mg (1.11 mmoles) of (4-bromophenyl)perfluorohexyl sulfone, and 20 mg (0.17 mmoles) of Pd(PPh3)4. To this clear colorless solution was added 170 mg (1.12 mmoles) of 4-methoxyphenylboronic acid in 2 ml of methanol, 240 mg (2.26 mmoles) of Na2CO3 in 1 ml of water. The mixture was stirred under nitrogen at 80° C. overnight. Isolation in accordance with the procedure of Example 9 gave after flash chromatography (silica gel, 50% CHCl3 /hexane) 343 mg of the biphenyl (0.60 mmoles, 54.6%). Elemental analyses: Found: C: 40.29; H: 2.03; calculated for C19H11F13O3S: C: 40.30; H: 1.96 Mp: 101.5°-103° C. SHG: not active. 1H nmr (CD2Cl2): 8.05 (d, J=8.6 Hz, 2H), 7.87 (d, J=8.6Hz, 2H), 7.65 (d, J=8.8 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 3.87 (s 3H).

Provenance & Evidence