Sodium Carbonate → 3-fluoro-4-methyl-2'-(N-triphenylmethyl-1H-tetrazol-5-yl)biphenyl

Participants

Reaction Steps

4-Bromo-2-fluorotoluene (5.00 g, 26 mmol, 1 eq), 2-(N-triphenylmethyl-1H-tetrazol-5-yl)benzeneboronic acid (U.S. Pat. No. 5,130,439) (14.29 g, 26 mmol, 1 eq), tetrakistriphenylphosphinepalladium (0) (1.53 g, 1.3 mmol, 0.05 eq), tetrabutylammonium bromide (0.42 g, 1.3 mmol, 0.05 eq), 2M sodium carbonate (28.99 mL, 58 mmol, 2.23 eq) and toluene (200 mL) were mixed and refluxed for 4 hours. The reaction was worked up as in example 1, part D to yield 11.98 g of an amber glass. The glass was dissolved in ethyl acetate (25 mL) and triturated with ether to yield 6.04 g of white solid product. The filtrate was concentrated and flash chromatographed in 9:1 hexanes/ethyl acetate to yield a further 3.72 g of white solid product. NMR (CDCl3) δ 8.00-7.85 (m, 1H); 7.55-7.40 (m, 2H); 7.40-7.10 (m, 10H); 7.00-6.70 (m, 9H); 2.18 (s, 3H). ##STR55##

Provenance & Evidence