𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Carbonylation of benzyl bromide to benzeneacetic acid and its esters catalysed by water-soluble palladium complexes

✍ Scribed by Anna M Trzeciak; Józef J Ziółkowski


Publisher
Elsevier Science
Year
2000
Tongue
English
Weight
152 KB
Volume
154
Category
Article
ISSN
1381-1169

No coin nor oath required. For personal study only.

✦ Synopsis


Ph PCH CH C O NHC CH CH SO Li in waterrtoluene solution exhibits activity in the carbonylation of benzyl 2 2 2 3 2 2 3

Ž . bromide to benzeneacetic acid 87% yield at 1308C and 10 atm of CO. In a reaction carried out in waterralcohol solution, corresponding esters were obtained in yields dependent on the kind of alcohol used: 24% for BuOH, 62% for i PrOH, 78%

Ž . for EtOH, and 85% for MeOH. In the synthesis of benzeneacetic acid methyl ester C H CH C O OCH at 50-1008C under 6 5 2 3

Ž . 5-10 atm of CO, TOF ca. 300 was achieved. The contribution of palladium 0 phosphine complexes was proved using the 31 Ä 1 4 Ž. Ž . P H NMR and IR methods. The complex Pd PNS , obtained in the reaction of PdCl cod with PNS and NaBH , reacts 4 2 4 Ž . Ž . 31 Ä 1 4 with C H CH Br yielding an oxidative addition product, PdBr C H CH PNS , identified using the P H NMR 6 5 2 6 5 2 2 Ž . method. In CD OD solution containing Pd PNS and C H CH Br saturated with CO, the ester described by the formula 3 4 6 5 2 Ž .


📜 SIMILAR VOLUMES