ChemicalBook CAS DataBase List 1-(2-bromo-5-methoxy-phenyl)ethanone

1-(2-bromo-5-methoxy-phenyl)ethanone synthesis

12synthesis methods

Product Name:1-(2-bromo-5-methoxy-phenyl)ethanone
CAS Number:6342-63-8
Molecular formula:C9H9BrO2
Molecular Weight:229.07

Obtained by action of pyridinium chlorochromate with 1-(2-bromo-5-methoxy) ethanol.

544-97-8 Synthesis

544-97-8
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$150.00/5g

56658-04-9
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$310.00/50g

6342-63-8
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$31.00/250mg

Yield:6342-63-8 99%

Reaction Conditions:

in toluene at 0 - 20; for 0.5 h;

Steps:

1; 10

Preparation of 1-(2-bromo-5-methoxy-phenyl)-ethanone (108): EPO [0194] To an ice cold solution of 8.75 g (35 mmol) 2-bromo-5-methoxy-benzoy1 chloride in 40 niL toluene, 9.63 mL (19.25 mmol) of a 2M toluene solution of dimethylzinc was added under argon atmosphere (dimethylzinc is pyrophoric - contact with air should be avoided.). The ice bath was removed and the mixture slowly warmed up to room temperature. Once the reaction starts it proceeds rapidly resulting in a turbid solution. The reaction was complete in 30 minutes. It was then cooled back to 0 °C and was quenched by adding 10 mL ethanol. The mixture was evaporated to dryness, the residue was dissolved in a mixture of 50 mL IM HCl and 100 mL ethyl acetate. The organic phase was separated and washed with 50 mL water (2x), brine (2x) and was dried (Na₂SO₄). The final solution was evaporated and the oil dried overnight in high vacuum to give 7.96 g (99%) of the title compound as a colorless liquid; ¹H-NMR (CDCl₃): δ (ppm) 7.46 (d, 1H), 6.96 (d, 1H), 6.83 (dd, 1H), 3.80 (s, 3H), 2.63 (s, 3H).

References:

WO2006/76529,2006,A1 Location in patent:Page/Page column 92; 93-94