Methyl 2-ethyl-2-(methoxymethyl)-[1,1-biphenyl]-4-carboxylate synthesis
- Product Name:Methyl 2-ethyl-2-(methoxymethyl)-[1,1-biphenyl]-4-carboxylate
- CAS Number:1196973-59-7
- Molecular formula:C18H20O3
- Molecular Weight:284.35
1141473-84-8
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Yield:1196973-59-7 83%
Reaction Conditions:
with potassium carbonate;tetrakis(triphenylphosphine) palladium(0) in water;toluene at 100; for 12 h;Inert atmosphere;Suzuki-Miyaura coupling;
Steps:
1
methyl 2'-ethyl-2-(methoxymethyl)-1 , 1 '-biphenyl-4-carboxylate To a solution of methyl 4-bromo-3-(methoxymethyl)benzoate, (Intermediate 28, step 2) (12 g, 0.0463 mol) in toluene (150 ml_) and water (35 ml_) under N2, was added 2-ethyl benzene boronic acid (9.02 g, 0.0601 mol) followed by potassium carbonate (19 g, 0.1389 mol) and Pd(PPh3)4 (2.67g, 0.0023 mol). The reaction mixture was degassed with N2 for 10 min before heating. After 12 hours at 1000C, the reaction mixture was diluted with EtOAc. The organic layer was washed with sodium bicarbonate sat. solution (1x100 ml_), water (2x100 ml_) and finally with brine (1x100 ml_). It was then dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography (silica gel, 60-120 mesh, eluting with pet ether/ EtOAc) to afford the title compound as a pale yellow liquid (12 g, 83%). 1H NMR (CDCI3, 400 MHz) δ 8.24-8.26 (1 H, s), 7.99-8.01 (1 H, d), 7.32-7.38 (2H, m), 7.22- 7.27 (2H, m), 7.07-7.09 (1 H, d), 4.12-4.21 (2H, d), 3.93-3.95 (3H, s), 3.28-3.30 (3H, s), 2.28- 2.43 (2H, m), 1.01-1.05 (3H, t).
References:
WO2010/69949,2010,A1 Location in patent:Page/Page column 71
148547-19-7
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