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. Author manuscript; available in PMC: 2011 Dec 22.
Published in final edited form as: Tetrahedron Lett. 2010 Dec 22;51(51):6748–6752. doi: 10.1016/j.tetlet.2010.10.087

Table 1.

Effect of irradiation time on benzyl 3,5-bis(benzloxy)-4-bromobenzoate (1)

Entrya Time 1:3:4b Yield of 3c
1 10 min × 2 0:1:trace 45
2 10 min × 3 0:1:trace 49
3 15 min × 2 0:1:trace 48
4 15 min 11:50:1 n/a
5 20 min 0:1:trace 57
6 30 min 0:1:trace 57
7 45 min 0:1:trace 56
8 60 min 0:1:trace 56
a

9 mol % PdCl2(dppf)CH2Cl2, THF:H2O (10:1) at 0.051 M, 5 equiv of 2, 3 equiv Cs2CO3, 150 °C.

b

Determined by 1H NMR integration of the crude mixture.

c

Isolated yield.