ChemicalBook CAS DataBase List 3-BROMO-5-METHOXYBENZALDEHYDE

3-BROMO-5-METHOXYBENZALDEHYDE synthesis

5synthesis methods

Product Name:3-BROMO-5-METHOXYBENZALDEHYDE
CAS Number:262450-65-7
Molecular formula:C8H7BrO2
Molecular Weight:215.04

199177-26-9
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262450-65-7
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$6.00/100mg

Yield: 91%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide at 0 - 20;

Steps:

15.15A Example 1 5A: 3 -Bromo-5-methoxybenzaldehyde
Example 1 5A: 3 -Bromo-5-methoxybenzaldehyde j00295j 3-Bromo-5-hydroxybenzaldehyde (0.5 g, 2.487 mmol) was dissolved in DMF(14.63 mL) and cooled to 0 °C. NaH (0.119 g, 4.97 mmol) was added in three portions.The flask was immediately allowed to warm to ambient temperature and Mel (0.93 3 mL,14.92 mmol) was added, and the reaction stirred overnight. The reaction was diluted with water and partially concentrated in vacuo. The material was diluted with DCM and washed twice with water, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (gradientfrom 0 to 100% EtOAc in hexanes) to yield Example 15A (0.488 g, 2.27 mmol, 9 1%).‘H NMR (400 MHz, CHLOROFORM-cl) ö ppm 9.91 (1 H, s), 7.58 (1 H, t, J=1.38 Hz), 7.28 - 7.35 (2 H, m, J=2.38, 2.13, 2.01, 2.01 Hz), 3.86 (3 H, s).

References:

BRISTOL-MYERS SQUIBB COMPANY;RICHTER, Jeremy;BATES, J. Alex;CHENEY, Daniel L. WO2014/201073, 2014, A1 Location in patent:Paragraph 00295