2-Bromo-1-(4-fluorophenyl)ethan-1-one → 4-(4-Fluorophenyl)oxazole
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH:12]([O-:14])=O.[NH4+:15]>C(O)=O>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:15]=[CH:12][O:14][CH:2]=2)=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Bromo-1-(4-fluoro-phenyl)-ethanone (10 grams, 46 mmol), ammonium formate (11 grams, 175 mmol) and formic acid (60 mL) were added to a flask. The mixture was heated to reflux for 3.5 hours. The reaction was then cooled and quenched with 200 mL water. The pH was adjusted to 8 with 50% aqueous sodium hydroxide, and the aqueous layer was extracted with methylene chloride (3×200 mL). The combined organic extracts were dried over sodium sulfate, and concentrated under vacuum. The crude, red solid obtained was choursomatographed on silica gel (ISCO MPLC purification, 50 minutes., 0-25% ethyl acetate gradient, Biotage flash 40 m column) to provide 1.62 grams (22%) of the title compound. MS m/z: ESI+ 164.1 (M+H)+.