ChemicalBook CAS DataBase List 2-BROMO-2'-METHOXYACETOPHENONE

2-BROMO-2'-METHOXYACETOPHENONE synthesis

5synthesis methods

Product Name:2-BROMO-2'-METHOXYACETOPHENONE
CAS Number:31949-21-0
Molecular formula:C9H9BrO2
Molecular Weight:229.07

Also obtained according to the procedure of Buckman (80%).

579-74-8 Synthesis

579-74-8
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$6.00/1g

31949-21-0
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$34.00/5g

Yield:31949-21-0 96%

Reaction Conditions:

with copper(ll) bromide in chloroform;ethyl acetate at 70; for 8 h;Inert atmosphere;Reflux;

Steps:

2-Bromo-1-(2-Methoxyphenyl)Ethanone (7a).

Copper (II) bromide (2.97 g, 6.66 mmol) was placed in a twonecked round-bottomed flask fitted with a reflux condenser. EtOAc (10.0 mL) was added to it and the mixture was stirred at 70C for 5 min under nitrogen atmosphere. 1-(2-Methoxyphenyl)ethanone (6) (0.50 g, 3.33 mmol) in CHCl3 (10.0 mL) was slowly added to it and then the mixture was refluxed for 8 h. After completion of the reaction, it was cooled to room temperature, filtered through Celite pad, and washed with EtOAc (20 mL). The filtrate was concentrated under reduced pressure. The crude was puri- fied by column chromatography (EtOAc:hexane = 1:4) to afford the pure product 7a (0.73 g, 96%) as brown liquid. Rf = 0.43 (EtOAc/hexane = 1/4); 1 H NMR (300 MHz, CDCl3): δ 7.81 (1H, dd, J = 7.8, 1.8 Hz), 7.52 (1H, td, J = 7.8, 1.8 Hz), 7.05-6.96 (2H, m), 4.61 (2H, s), 3.94 (3H, s); 13C NMR (75 MHz, CDCl3): δ 192.3, 158.8, 134.9, 131.6, 124.9, 121.2, 111.7, 56.0, 38.0.

References:

Jang, Ha Young;Damodar, Kongara;Kim, Jin-Kyung;Jun, Jong-Gab [Bulletin of the Korean Chemical Society,2017,vol. 38,# 12,p. 1481 - 1485]