5-BENZYLOXY-2-BROMOBENZALDEHYDE

Synthesis of (1E, 6E)-1-(5-benzyloxy-2-bromophenyl)-7-(4-hydroxyphenyl)hepta-1, 6-diene-3, 5-dione (CU531); (1) Synthesis of 5-benzyloxy-2-bromobenzaldehyde; To a suspension of 2-bromo-5-hydroxybenzaldehyde (100 mg, 0.50 mmol), potassium carbonate (138 mg, 1.00 mmol), and tetrabutylammonium iodide (18 mg, 0.05 mmol) in 1.0 mL of dry N, N-dimethylformamide was added benzyl bromide (89 μL, 0.74 mmol) at 0°C. After being stirred at room temperature overnight, the reaction mixture was diluted with diethyl ether, and the solution was washed with water, saturated NaHCOTo a suspension of 2-bromo-5-hydroxybenzaldehyde (100 mg, 0.50 mmol), potassium carbonate (138 mg, 1.00 mmol), and tetrabutylammonium iodide (18 mg, 0.05 mmol) in 1.0 mL of dry N, N-dimethylformamide was added benzyl bromide (89 μL, 0.74 mmol) at 0° C.201 g (1 mol) of 2-bromo-5-hydroxybenzaldehyde, 1000 ml of acetone, and 276 g of potassium carbonate (1.1 mol) were added to the reaction vessel, and 152 g (1.2 mol) of benzyl chloride was added thereto with stirring, and the mixture was refluxed for 10 hours to recover a solvent. Add 1000ml water, beaten, filter, reducePress drying to obtain 279 g of solid, yield 96percent;General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1, 10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).

Molecular Weight:291.14
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:289.99424
Monoisotopic Mass:289.99424
Topological Polar Surface Area:26.3
Heavy Atom Count:17
Complexity:238
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes