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. Author manuscript; available in PMC: 2012 Sep 30.
Published in final edited form as: Tetrahedron. 2011 Sep 30;67(39):7461–7469. doi: 10.1016/j.tet.2011.07.064

Table 3.

Iodination of phenol (1a) and 3,5-dichlorophenol (1b) using different iodination reagents.*

graphic file with name nihms315974u3.jpg
Entry Reaction Conditionsa Reaction time (h) Conversion (%) Yield
2 (%) 3 (%) 4 (%)
(A) Phenol (1a)
3-1 AgSbF6, I2, DCM 23 79 2 1 T
3-2 AgBF4, I2, DCM 1.5 100 7 3 T
3–3 AgPF6, I2, DCM 23 91 4 46 T
(B) 3,5-Dichlorophenol (1b)
3–4 Ag2SO4, I2, DCMb 16 100 53 2 T
3–5 AgSbF6, I2, DCM 16 <100 82 T nd
3–6 AgBF4, I2, DCMc 1 <100 >90 5 nd
3–7 AgPF6, I2, DCM 16 <100 57 10 nd
*

Percent conversion and yields were determined by GC-MS;

a

one equivalent (eq.) of each reagent was employed if not mentioned otherwise;

b

I2 (1.5 eq.) and Ag2SO4 (1.5 eq.);

c

I2 (1.1 eq.) and Ag2SO4 (1.1 eq.);

T = traces were detected by GC-MS; nd = not detected.