Benzoic Acid → HCID 21956516, compound

Participants

Reaction Conditions

Reaction Steps

N,3-dimethyl-N,4-bis(methyloxy)benzamide (Prepared from the corresponding benzoic acid following the standard literature procedure for the formation of Weinreb amide, 6.2 g, 29.6 mmol) was dissolved in anhydrous THF (110 mL) under nitrogen and the solution was cooled to 0° C. A solution of 3 M phenyl magnesium bromide in ether (15.0 mL, 44.4 mmol) was then added drop-wise while maintaining an internal temperature of 0° C. to 5° C. The resulting mixture was stirred for 3 h at 0° C. to 5° C. then quenched with 5% aqueous HCl (150 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuuo to give 9.2 g of the crude 39 that was used without additional purification. 1H NMR (400 MHz, CDCl3): δ 2.13 (s, 3H), 3.92 (s, 3H), 6.91 (d, J=8.8 Hz, 1H), 7.40-7.62 (m, 5H), 7.64-7.70 (m, 1H), 7.73-7.79 (m, 1H).

Provenance & Evidence