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ChemicalBook CAS DataBase List 1-(5-Fluoro-2-hydroxyphenyl)-1-ethanone
394-32-1

1-(5-Fluoro-2-hydroxyphenyl)-1-ethanone synthesis

11synthesis methods
Preparation by Fries rearrangement of 4-fluorophenyl acetate with aluminium chloride without solvent between 115° and 150° (88–89%).
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Yield:394-32-1 98.4%

Reaction Conditions:

with aluminum (III) chloride at 130; for 2 h;

Steps:

7.1 Step 1: synthesis of 1- (5-fluoro-2-hydroxyphenyl) ethanone
4-Fluorophenol (72.00 g, 642.0 mol) was added into a three-neck flask, and stirred at 0 , then acetyl chloride (57.50 g, 732.0 mmol) was added dropwise slowly into the flask. After dropwise addition, the mixture was stirred at 25 for 2 h, then heated to 130 , and anhydrous aluminium trichloride (111.50 g, 835.0 mmol) was added slowly into the mixture. After addition, the resulting mixture was stirred at 130 for 2 h, then to the mixture was added water (500 mL) with stirring. The mixture was extracted with ethyl acetate (300 mL) for three times, and the combined organic layers were concentrated in vacuo to remove the solvent and give a brown solid (97.30 g) , yeild: 98.4%.[0497]MS-ESI: m/z 153.1 [M-H]-.

References:

DONGGUAN HEC TECH R & D CO., LTD.;LI, Yitao;CHI, Weilin;ZENG, Shuiming;LIAN, Zeyu;ZHANG, Hu;LIN, Jian WO2019/62802, 2019, A1 Location in patent:Paragraph 00228

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