ChemicalBook CAS DataBase List 3'-BROMO-4'-METHYLACETOPHENONE

3'-BROMO-4'-METHYLACETOPHENONE synthesis

8synthesis methods

Product Name:3'-BROMO-4'-METHYLACETOPHENONE
CAS Number:40180-80-1
Molecular formula:C9H9BrO
Molecular Weight:213.07

122-00-9 Synthesis

122-00-9
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$5.00/25g

40180-80-1
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$23.00/1g

Yield:40180-80-1 93%

Reaction Conditions:

Stage #1:para-methylacetophenone with aluminum (III) chloride in dichloromethane at 0; for 0.666667 h;Inert atmosphere;Schlenk technique;Glovebox;
Stage #2: with bromine in dichloromethane at 20; for 1 h;Inert atmosphere;Schlenk technique;Glovebox;

Steps:

3-Bromo-4-methylacetophenone
A solution of 97 g (723 mol) of 4-methylacetophenone in 100 ml of dichloromethane was added by vigorous stirring over 30 min to a suspension of 237 g (1.78 mol) of AlCl₃ in 700 ml of dichloromethane at 0 °C. The reaction mixture was then stirred for 10 min at this temperature, then 40.0 ml (125 g, 0.781 mol, 8% excess) of bromine was added dropwise over 1 h. The resulting mixture was stirred overnight at room temperature and then poured onto 2000 cm³ of ice. The organic layer was separated, and the aqueous layer was extracted with 3 x 150 ml ofdichloromethane. The combined organic extract was washed with aqueous K2CO₃, dried over K₂CO₃, passed through a short pad of silica gel 60 (40-63 μιη), and then evaporated to dryness. Crude product was distilled under vacuum to give 143 g (93%) of a colorless liquid (b.p. 125-132 °C/8 mm Hg) which completely solidified on standing at room temperature.

References:

BOREALIS AG;RESCONI, Luigi;VIRKKUNEN, Ville;NOUREDDINE, Ajellal;CASTRO, Pascal;IZMER, Vyatcheslav;KONONOVICH, Dmitry;VOSKOBOYNIKOV, Alexander WO2014/96282, 2014, A1 Location in patent:Page/Page column 44; 45

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536-50-5 Synthesis