2-IODO-4-(TRIFLUOROMETHOXY)PHENOL synthesis

Yield:405517-54-6 96%

Reaction Conditions:

with N-iodo-succinimide;sulfuric acid;glacial acetic acid at 20; for 48 h;

Steps:

2.1; 3.1 Synthesis of 2-iodo-4-(trifluoromethoxy) phenol (C13)

4-(Trifluoromethoxy)phenol (4.0 mL, 31 mmol) was added to a suspension of N-iodosuccinimide (95%, 6.95 g, 29.3 mmol) in acetic acid (2.0 mL, 35 mmol), and the mixture was stirred for 5 minutes. Sulfuric acid (98%, 0.5 mL, 9 mmol) was introduced, and stirring was continued at room temperature for 48 hours, whereupon the reaction mixture was poured into water (100 mL) and extracted with diethyl ether. The combined organic layers were washed with water, washed twice with 1 M aqueous sodium thiosulfate solution, treated with decolorizing carbon, and dried over magnesium sulfate. After the mixture had been filtered through a pad of diatomaceous earth and silica gel, the filtrate was concentrated in vacuo to provide the product as an oil (13.2 g). By ¹H NMR analysis, this product contained a significant quantity of ethyl acetate. Yield, corrected for ethyl acetate: 8.5 g, 28 mmol, 96%. ¹H NMR (400 MHz, CDCl₃) δ 7.54 (br d, J=2.6 Hz, 1H), 7.15 (br dd, J=8.9, 2.6 Hz, 1H), 6.99 (d, J=8.9 Hz, 1H).

References:

US2016/222007,2016,A1 Location in patent:Paragraph 0302; 0303