2-Propenoyl chloride, 3-[4-(1,1-dimethylethyl)phenyl]- synthesis

Yield:78974-03-5 99%

Reaction Conditions:

with oxalyl dichloride in dichloromethane at 0 - 20; for 5 h;

Steps:

Synthesis of (E)-3-(4-(tert-butyl)phenyl)acryloyl chloride 68S20

To a stirred solution of the appropriate acid 3a-d (6 mmol) in DCM (50 mL) was added oxalyl chloride (1 mL, 12 mmol), and the mixture was stirred at r.t. for 5h. The resulting solution was concentrated under reduced pressure to give the desired product, which was used for the next step without further purification.Same as described above for acryloyl chlorides 4a-d. Obtained in 99% yield as a white solid.1H-NMR (CDCl3), δ: 1.37 (s, 9H), 6.64 (d, J = 15.5 Hz, 1H), 7.48 (d, J= 8.4 Hz, 2H), 7.54 (d, J= 8.4 Hz, 2H), 7.85 (d, J= 15.5 Hz, 1H). 13C-NMR (CDCl3): δ: 31.1, 31.1, 121.3, 126.2, 130.3, 150.7, 128.4, 156.0, 166.1.

References:

Giancotti, Gilda;Cancellieri, Michela;Balboni, Andrea;Giustiniano, Mariateresa;Novellino, Ettore;Delang, Leen;Neyts, Johan;Leyssen, Pieter;Brancale, Andrea;Bassetto, Marcella [European Journal of Medicinal Chemistry,2018,vol. 149,p. 56 - 68] Location in patent:supporting information