Table 3.

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

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;

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

^bI₂ (1.5 eq.) and Ag₂SO₄ (1.5 eq.);

^cI₂ (1.1 eq.) and Ag₂SO₄ (1.1 eq.);

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