[1,1'-Biphenyl]-4-carboxylic acid, 4'-(trifluoroMethyl)-, Methyl ester synthesis

10synthesis methods

Product Name:[1,1'-Biphenyl]-4-carboxylic acid, 4'-(trifluoroMethyl)-, Methyl ester
CAS Number:127783-73-7
Molecular formula:C15H11F3O2
Molecular Weight:280.24

619-42-1 Synthesis

619-42-1
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$7.00/10g

128796-39-4 Synthesis

128796-39-4
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$10.00/5g

[1,1'-Biphenyl]-4-carboxylic acid, 4'-(trifluoroMethyl)-, Methyl ester

127783-73-7
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$400.00/1g

Yield:127783-73-7 92%

Reaction Conditions:

with triphenylphosphine;cesium fluoride;palladium diacetate in methanol;1,2-dimethoxyethane; for 24 h;Heating / reflux;Suzuki Coupling;

Steps:

1.A'

A suspension of 4- (trifluoromethyl)phenylboronic (7.3 g, 38.4 mmol), methyl 4-bromobenzoate (7.44 g, 36.4 mmol), triphenylphosphine (1.21g, 4.6 mmol), cesium fluoride ( 11.7 g, 76.8 mmol) and palladium acetate (0.26 g, 1.15 mmol) in degassed DME and methanol is heated at reflux for 24h. The suspension is cooled to room temperature, filtered, and the resulting filtrate concentrated in vacuo to give a dark .solid. This material is taken up in acetone and adsorbed on silica gel, and purified by flash filtration using 500 mL each of 2% to 20% ethyl acetate/hexanes in 2% increments. Fractions containing the product are combined to give the title compound in 92% yield. NMR (CDC13) 8.10 (d, J= 8.4 Hz, 2H), 7.99 (d, J=7.9 Hz, 2H), 7.92 (d, J= 8.4Hz, 2H), 7.83 (d, 8.4 Hz, 2H), 3.58 (s, 3H).

References:

WO2005/97740,2005,A1 Location in patent:Page/Page column 27

1126-46-1 Synthesis