4-Fluorophenol → HCID 59753961, compound

Participants

Reaction Conditions

Reaction Steps

To a 5 mL round bottom flask fitted with a stirrer bar and septum was added 2 mL CH3CN and 2-methylsulfonyl-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine from from Reference Example 3 (100 mg, 0.24 mmol). Then 4-fluorophenol (10 eq., 269 mg, 2.4 mmol), K2CO3 (2 eq., 66.3 mg, 0.48 mmol) and a drop of tris[2-(2-methoxyethoxy)-ethyl]amine were added via syringe and the mixture heated at 70° C. for 2 h. By HPLC/MS, the starting material was converted to the desired product. The product was extracted from 10 mL water with 20 mL ethyl acetate, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. Flash column chromatography on silica gel (eluted with 90/10 hexanes/ethyl acetate) afforded 2-(4-fluorophenyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine: HPLC/MS: m/e=445 (M++1); Rt=4.53 min; 1H-NMR 400 MHz (CDCl3): δ 7.02 (d, J=9 Hz, 2H), 7.20-7.40 (m, 9H), 8.80 (s, 1H).

Provenance & Evidence