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. Author manuscript; available in PMC: 2008 Sep 12.
Published in final edited form as: J Org Chem. 2006 Jan 6;71(1):142–149. doi: 10.1021/jo0518809

Table 2.

Screening of solvents and basesa

graphic file with name nihms63112f9.jpg
entry base solvent T (°C) yield (%)b
1 K2CO3 n-butanol 117 75
2 K2CO3 water 100 35
3 K2CO3 ethylene glycol 130 40
4 K2CO3 2-ethoxyethanol 130 76
5 K2CO3 diethylene glycol 130 90
6 Cs2CO3 diethylene glycol 130 5
7 Na2CO3 diethylene glycol 130 82
8 tert-BuOK diethylene glycol 130 11
9 K3PO4 diethylene glycol 130 70
10 NaOAc diethylene glycol 130 66
11 TMP diethylene glycol 130 30
12 Na2CO3 2-ethoxyethanol 130 92d
13 K2CO3 2-ethoxyethanol 130 75c
14 K2CO3 2-ethoxyethanol 130 83c,d
a

Reaction conditions: 2-Chlorobenzoic acid (1.38 g, 8.83 mmol), 1.05 equiv. of 2-methylaniline, 9 mol% of Cu, 4 mol% of Cu2O, 2.0 equiv. of base, 3 mL of solvents, 130°C for 24 hours.

b

Isolated yields.

c

Aniline was used.

d

1.0 equiv. of base was used.