ChemicalBook CAS DataBase List 3'-METHOXY-BIPHENYL-2-CARBALDEHYDE

3'-METHOXY-BIPHENYL-2-CARBALDEHYDE synthesis

8synthesis methods

Product Name:3'-METHOXY-BIPHENYL-2-CARBALDEHYDE
CAS Number:38491-36-0
Molecular formula:C14H12O2
Molecular Weight:212.24

10365-98-7 Synthesis

10365-98-7
405 suppliers
$9.00/10g

6630-33-7
407 suppliers
$9.00/10g

38491-36-0
15 suppliers
$234.00/1g

Yield:38491-36-0 99%

Reaction Conditions:

with tripotassium phosphate tribasic;palladium diacetate in tetrahydrofuran;water monomer at 110; for 15 h;Inert atmosphere;Schlenk technique;

Steps:

3'-Methoxy-[1,1'-biphenyl]-2-carbaldehyd (26):

Prepared according to a modified literature procedure by Potter and co-workers.4 2-Bromobenzaldehyde (3.7 g, 20 mmol, 1.0 equiv) and 3-methoxyboronic acid (3.80 g, 25.0 mmol, 1.25 equiv) were placed in a reaction vessel and dissolved in a mixture of tetrahydrofuran (120 mL) and aq. K3PO4 (2M, 15 mL). The reaction mixture was degassed using a freeze-pump-thaw procedure (3x), after which palladium(II) acetate (89.8 mg, 400 μmol, 0.02 equiv) was added. The mixture was heated to 110°C in an oil bath at reflux for 15 h. After cooling to room temperature, dest. H2O (30 mL) was added, and the aqueous layer extracted with EtOAc (3 x 100 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica gel using cyclohexane:EtOAc = 20:1 as eluent afforded 26 as a yellow oil (4.21 g, 19.8 mmol, 99%).

References:

Gross, Benjamin M.;Oestreich, Martin [Synthesis,2021,vol. 53,# 14,p. 2512 - 2516] Location in patent:supporting information

2398-37-0 Synthesis