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ChemicalBook CAS DataBase List 2-Bromo-1-(3-fluorophenyl)ethan-1-one
53631-18-8

2-Bromo-1-(3-fluorophenyl)ethan-1-one synthesis

4synthesis methods
3'-Fluoroacetophenone

455-36-7

2-Bromo-1-(3-fluorophenyl)ethan-1-one

53631-18-8

GENERAL METHODS: Oxone (1.352 g, 2.2 mmol) was added to a well-stirred methanol (10 mL) solution of m-fluoroacetophenone (2 mmol) and NH4Br (0.215 g, 2.2 mmol) and the reaction mixture was stirred at room temperature (or reflux temperature). The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was quenched with aqueous sodium thiosulfate and extracted with ethyl acetate (3 × 25 mL). The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum to remove the solvent to give the crude product. The crude product was further purified by silica gel column chromatography (200-300 mesh) to give pure 2-bromo-3'-fluoroacetophenone. All products were structurally confirmed by 1H NMR and mass spectrometry data.

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Yield:53631-18-8 93%

Reaction Conditions:

with water in 1,2-dichloro-ethane at 20; for 14 h;

Steps:

General procedure for the synthesis of a-halomethyl ketones

General procedure: To a solution of haloalkyne (0.5 mmol) in DCE (5 mL) were added H2O (27 mg,1.5 mmol) and MCM-41-PPh3-AuNTf2 (58 mg, 0.015 mmol). The reaction mixture was stirred at room temperature and the progress of the reaction was monitored using TLC.The reaction typically took 14 h. After completion of the reaction, the catalyst was separated by a simple filtration of the reaction solution, washed with acetone (25 mL),and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified using chromatography on silica gel (eluent: light petroleumether/ethyl acetate =25: 1) to afford the desired product 2a-2b’.

References:

Hu, Sifan;Liu, Dayi;Yan, Chenyu;Cai, Mingzhong [Synthetic Communications,2018,vol. 48,# 23,p. 2983 - 2991] Location in patent:supporting information

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