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

863870-77-3

858854-82-7

Step 3: Sodium hydroxide (32.0 g, 800 mmol) was slowly added to a 400 mL ethanol solution containing 3-chloro-2-iodophenyl N,N-diethylcarbamate (57.0 g, 161 mmol) at 25 °C. The reaction mixture was heated to reflux and maintained for 2 hours. Upon completion of the reaction, the ethanol solvent was removed by distillation under reduced pressure. The residue was dissolved in 400 mL of water and subsequently extracted with petroleum ether. The aqueous phase was neutralized with 2N hydrochloric acid solution and extracted with ethyl acetate. All organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. Finally, the organic solvent was removed by distillation under reduced pressure to afford the target product 3-chloro-2-iodophenol (41.0 g, quantitative yield). The product was characterized by 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).

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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