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ChemicalBook CAS DataBase List 5-Bromo-2-ethylbenzaldehyde
946001-65-6

5-Bromo-2-ethylbenzaldehyde synthesis

3synthesis methods
22927-13-5 Synthesis
2-ETHYLBENZALDEHYDE

22927-13-5
97 suppliers
$16.00/1g

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Yield:946001-65-6 58%

Reaction Conditions:

Stage #1: 2-ethylbenzaldehydewith aluminum (III) chloride;bromine in dichloromethane at 0 - 20; for 22 h;
Stage #2: with water in dichloromethane at 0;

Steps:



5-Bromo-2-ethyl-benzaldehyde (235)A stirred suspension of 2-ethylbenzaldehyde (0.98 mL, 7.45 mmol) and AlCl3 (1.74 g, 13 mmol) in DCM (4.5 mL) at 0°C is treated with a solution of Br2 (0.38 mL 7.45 mmol) in DCM (4.5 mL) dropwise over 6 h then stirred 16 h at RT. After this time, EPO the reaction mixture is poured over ice-water (50 mL), the layers separated and the aqueous layer extracted with DCM (3 x 50 mL). The organic phases are combined and washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4 then the solvents removed in vacuo. Purification by column chromatography (gradient elution - 100% heptane increasing to 10% EtOAc in heptane) gives the title compound. Yield: 925 mg (58%). LC/MS tr 1.55 min. MS(ES+) m/z mass ion not detected.

References:

WO2008/57497,2008,A2 Location in patent:Page/Page column 362-363

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