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. Author manuscript; available in PMC: 2011 Jul 11.
Published in final edited form as: Angew Chem Int Ed Engl. 2010 Nov 8;49(46):8729–8732. doi: 10.1002/anie.201004426

Table 1.

Optimization of ortho-halogenation reaction. X =halide.

graphic file with name nihms304130u1.jpg
Entry Additive (equiv) Hal Solvent T [8C] Yield [%][a]
1 none Br PrCN 80 50
2 none Br PrCN 100 65
3 AcOH (50) Br PrCN 80 15
4 Cu(OAc)2 (1) Br PrCN 100 trace
5 PhI(OAc)2 (1.5) Br PrCN 80 80
6 PhI(OAc)2 (1.5) Br PrCN 100 65
7 PhI(OAc)2 (1.5) Br C2H4Cl2 60 85
8 PhI(OAc)2 (1.5) I C2H4Cl2 65 95
9 PhI(OAc)2 (1.5) Cl C2H4Cl2 65 42
[a]

Yield determined by NMR spectroscopy.