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
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✦ 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 .
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