ChemicalBook CAS DataBase List 3-CHLORO-2-IODOPHENOL

3-CHLORO-2-IODOPHENOL synthesis

7synthesis methods

Product Name:3-CHLORO-2-IODOPHENOL
CAS Number:858854-82-7
Molecular formula:C6H4ClIO
Molecular Weight:254.45

3-CHLORO-2-IODOPHENYL N,N-DIETHYLCARBAMATE

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Yield: 100%

Reaction Conditions:

with ethanol;sodium hydroxide at 25; for 2 h;Inert atmosphere;Reflux;

Steps:

21.c.3 Step 3
(c) Step 3
Sodium hydroxide (32.0 g, 800 mmol) was added at 25° C. to 400 mL of an ethanol solution of 3-chloro-2-iodophenyl N,N-diethylcarbamate (57.0 g, 161 mmol), and the reaction solution was heated and refluxed for two hours.
The ethanol was distilled off under reduced pressure, and the residue was dissolved in 400 mL of water and extracted by petroleum ether.
The water layer was neutralized by 2N hydrochloric acid, and extracted by ethyl acetate.
The combined organic layers were washed with (saturated) brine, dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 3-chloro-2-iodophenol (41.0 g, quantitative).
¹H NMR (400 MHz, CDCl₃) δ 5.58 (brs, 1H), 6.90 (dd, J=1.2, 8.4 Hz, 1H), 7.06 (dd, J=1.2, 8.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H).

References:

THE UNIVERSITY OF TOKYO;NAGANO, Tetsuo;NAKANO, Hirofumi;HASEGAWA, Tsukasa;SAITO, Nae;KOJIMA, Hirotatsu;OKABE, Takayoshi;MUKAIDA, Naofumi US2017/145005, 2017, A1 Location in patent:Paragraph 0368; 0375; 0376; 0377