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1038827-60-9

5-hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde synthesis

3synthesis methods
2973-80-0 Synthesis
2-BROMO-5-HYDROXYBENZALDEHYDE

2973-80-0
393 suppliers
$6.00/1g

5-hydroxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

1038827-60-9
32 suppliers
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Yield: 100%

Reaction Conditions:

with potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 in dimethyl sulfoxide at 70; for 16 h;

Steps:

71.a
Step (a) 5-hydroxy-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzaldehyde1 , 1 '-bis(diphenylphosphino)ferrocenedichloro-palladium(ii) dichloromethane complex (1.009 g, 1.24 mmol) and l,l'-bis(diphenylphosphino)ferrocene (0.685 g, 1.24 mrαol) were stirred in DMSO (40 mL) at rt. for 10 min. 2-bromo-5-hydroxybenzaldehyde (5.00 g, 24.87 mmol), potassium acetate (7.28 g, 74.18 mmol) and diboron pinacol ester (8.16 g, 32.14 mmol) were added under nitrogen. The reaction was stirred for 16 h at 7O0C, cooled and poured onto water (300 mL) . The resulting mixture was extracted into diethyl ether and washed with brine and dried over sodium sulfate to give the title compound (6.7g, 109%) as a purple gum. Used in the next step without purification or analysis

References:

ASTRAZENECA AB;ASTRAZENECA UK LIMITED WO2008/84223, 2008, A2 Location in patent:Page/Page column 144-145