N,N,N',N'-Tetramethylethylenediamine → 3-Methoxyaniline

The advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole, the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-t-Bu)PdCl2 (1 mol %) in DME gave a complicated mixture of products was obtained (Table 10, Entry 1). When conducted in the presence of zinc chloride and TMEDA, however, the reaction could successfully gave the desired monoarylation product, 3-methoxyaniline, although at high concentrations N,N-dimethyl-3-methoxyaniline was formed in a significant amount as a by-product (Table 10, Entries 3 and 4). Under optimized conditions (Table 10, Entries 8 and 9), 3-methoxyaniline was formed selectively in good yield.

1. customthe results of which
2. customgave
3. additiona complicated mixture of products
4. customwas obtained (Table 10, Entry 1)
5. customhowever, the reaction

ORD record

ord-3f73894ea6ed4a4e96212d38581009ea

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058477B2