Methyl 4-iodobenzoate → HCID 10619533, compound

Participants

Reaction Steps

To a solution of (2.9 g, 8.65 mmol, 1.0 eq) 1-methoxy-2-(4-phenyl-1-butoxy)-4-bromobenzene in 30 ml of dry THF at -78° C. was added (3.81 ml, 9.52 mmol, 1.1 eq) 2.5M n-BuLi. After stirring 15 minutes at -78° C. (10.4 ml, 10.4 mmol, 1.2 eq) 1.0M ZnCl2 in ether was added and the mixture allowed to warm to room temperature over 35 minutes. Tetrakis(triphenylphosphine)palladium(O) (500 mg, 0.43 mmol, 0.05 eq) and (2.27 g, 8.65 mmol, 1.0 eq) methyl-4-iodobenzoate were added to the reaction and the mixture allowed to stir at room temperature for 2.5 hours. The reaction mixture was concentrated in vacuo, costripped with CHCl3, and chromatographed on a silica gel column eluting with ethyl acetate-hexane (0-10%) to afford 2.61 g, 76%, of a yellow solid. Hydrolysis of the ester according to the method of Example 4 gave the title compound, M.P.: 178°-179° C. Elemental analysis calculated for C24H24O4 : C, 76.56; H, 6.43. Found: C, 76.06; H, 5.92.

Provenance & Evidence