Acetic Acid → HCID 74891939, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-BuLi (2.5 M in hexanes, 1.98 mL, 4.94 mmol) was added to a solution of diisopropylamine (0.700 mL, 4.94 mmol) in THF (10 mL) at −30° C. After 15 minutes, the mixture was cooled to −70° C., then 3-bromo-4-fluorobenzotrifluoride (1.00 g, 4.12 mmol) was added. After 30 minutes, anhydrous DMF (0.637 mL, 8.23 mmol) was added dropwise. After 15 minutes, acetic acid (0.50 mL, 8.2 mmol) was added, then the mixture was diluted with ethyl acetate and water. The resulting layers were separated, and the aqueous phase was extracted with ethyl acetate. The combined organics were washed with saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated. The resulting light yellow oil was used directly for the following step. 1H NMR (500 MHz, CDCl3) δ 10.38 (s, 1H); 8.10-8.15 (m, 2H). LC1: 3.44 min. Compound does not ionize.

Provenance & Evidence