Pivaloyl chloride → HCID 86719528, Verbindung

Beteiligte Stoffe

Reaktionsschritte

To a solution of (2-bromophenyl)diphenylphosphine (II-a) (0.50 mmol) in dry THF (2 mL) was added dropwise under argon at −78° C. n-BuLi (0.55 mmol). The resulting solution was stirred at this temperature during one hour and pivaloyl chloride (0.80 mmol) was then added dropwise. After stirring at room temperature overnight, the reaction mixture was quenched with water (10 mL) and extracted with methylene chloride (3×10 mL). The organic phases were dried over MgSO4, filtered and the solvent evaporated giving a residue which was purified by column chromatography on silica gel using petroleum ether/ethyl acetate 3:1 as eluent. White solid; Yield 78%; Rf 0.43 (petroleum ether/ethyl acetate 3:1); IR (neat) 3049, 2967, 2928, 2867, 1686, 1585, 1477, 1458, 1431, 1389, 1361, 1283, 1192, 967, 947, 778, 741, 691 cm−1; 1H NMR (300MHz, CDCl3) δ 1.35 (s, 9H, CH3), 7.18-7.22 (m, 1H, Harom), 7.25-7.40 (m, 13H, Harom); 13C NMR (75.5 MHz, CDCl3) δ 27.7 (d, J=3.3 Hz, CH3), 44.7 (C(CH3)3), 124.8 (d, J=8.6 Hz, Carom), 128.3 (Carom), 128.5 (d, J=4.9 Hz, Carom), 128.7 (Carom), 133.3 (Carom), 133.5 (Carom), 134.6 (d, J=15.8 Hz, Carom), 134.8 (d, J=2.2 Hz, Carom), 137.0 (d, J=10.4 Hz, Carom), 148.0 (d, J=35.8 Hz, Carom); 31P NMR (121 MHz, CDCl3) δ −10.4; HRMS calcd for C23H23PONa [M+Na]+369.1379, found 369.1382.

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