ChemicalBook CAS DataBase List 5-BROMO-2-ISOPROPOXYBENZALDEHYDE

5-BROMO-2-ISOPROPOXYBENZALDEHYDE synthesis

5synthesis methods

Product Name:5-BROMO-2-ISOPROPOXYBENZALDEHYDE
CAS Number:138505-25-6
Molecular formula:C10H11BrO2
Molecular Weight:243.1

75-30-9
265 suppliers
$15.00/1g

1761-61-1
382 suppliers
$5.00/5g

138505-25-6
49 suppliers
$58.00/250mg

Yield:138505-25-6 99%

Reaction Conditions:

with potassium carbonate;caesium carbonate in N-methyl-acetamide;

Steps:

29.A Synthesis of DArPhin Catalysts

Step A: Synthesis of 5-bromo-2-isopropoxybenzaldehyde AX. To a suspension of potassium carbonate (34.4 g, 249 mmol) and cesium carbonate (16.2 g, 50 mmol) in dimethylformamide were added 5-bromosalicaldehyde (25.0 g, 124 mmol) and 2-iodopropane (25.0 mL, 249 mmol). The suspension was stirred at room temperature overnight, then at 70° C. for 4 hrs. The volatiles were removed, and the residue was partitioned between methyl t-butylether and water. The aqueous layer was extracted with methyl t-butylether and the combined organic phases were washed with water, sodium hydroxide, and brine, and then dried over magnesium sulfate. Concentration to dryness afforded compound AX (30.0 g) as a pale yellow oil in 99% yield. ¹H NMR (CDCl₃, 400 MHz): δ 1.40 (d, J=6.3 Hz, 6H), 4.65 (sept., J=6.0 Hz, 1H), 6.89 (d, J=9.0 Hz, 1H), 7.59 (dd, J=9.0 and 2.7 Hz, 1H), 7.91 (d, J=2.7 Hz, 1H), 10.39 (s, 1H).

References:

US2009/202480,2009,A1