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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 1.

Effect of iodinating reagents, solvents and temperature on the iodination of 3,5-dichlorophenol (1b).*

graphic file with name nihms315974u1.jpg
Entry Reaction Conditionsa Reaction time (h) Conversion (%) Yield
2b (%) 3b (%) 4b (%)
1–1 I2 (1.5 eq.), C2H5OH 16 100 16 1 T
1–2 N-Iodosuccinimide, PTSA, CH3CN 24 < 100 18 57 T
1–3 BTMACl2I, ZnCl2, AcOH, RTb 24 < 100 5 4 nd
1–4 BTMACl2I, ZnCl2, AcOH, 90 °Cc 2 < 100 46 39 T
1–5 CAN, I2, CH3CN 24 > 0 2 2 nd
1–6 Ag2SO4, I2, CH3CNd 16 > 0 11 3 T
1–7 Ag2SO4, I2, DCM-MeOH-H2O (1:1:1, v/v)d 2 100 9 2 T
1–8 Ag2SO4, I2, β-cyclodextrine 1 100 8 nd nd
1–9 Ag2SO4, I2, n-hexaned 16 < 100 49 41 T
1–10 Ag(OCOCF3)2, I2, C2H5OH 16 < 100 28 4 T
*

Percent conversion and yields were determined by GC-MS;

a

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

b

BTMACl2I (1.5 eq.) and ZnCl2 (1.5 eq.);

c

BTMACl2I (1.1 eq.) and ZnCl2 (1.5 eq.);

d

I2 (1.5 eq.) and Ag2SO4 (1.1 eq.);

e

β-cyclodextrin in DMSO was added to a solution containing 1b and Ag2SO4/I2 (1 eq.: 1 eq.) in DCM (DMSO: DCM = 1: 1, v/v);

T = traces were detected by GC-MS; nd = not detected; BTMACl2I = benzyltrimethylammonium dichloroiodinate; RT = room temperature; PTSA = p-toluenesulfonic acid.