Cesium fluoride → 4'-(2-Hydroxyethoxy)-3',5'-dimethylbiphenyl-4-carboxylic acid

HRID 2220635Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]([CH3:12])[C:5]([O:6][CH2:7][CH2:8][OH:9])=[C:4]([CH3:13])[CH:3]=1.[C:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([OH:16])=[O:15].[F-].[Cs+].O1CCOCC1>C(OCC)(=O)C.O.C(O)C>[OH:9][CH2:8][CH2:7][O:6][C:5]1[C:10]([CH3:12])=[CH:11][C:2]([C:20]2[CH:21]=[CH:22][C:17]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)=[CH:3][C:4]=1[CH3:13]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(4-bromo-2,6-dimethylphenoxy)ethanol (0.645 g), 4-carboxyphenylboronic acid (0.873 g), tetrakis-(triphenylphosphine)palladium(0) (0.152 g), cesium fluoride (2.398 g), 1,4-dioxane (7.5 mL), ethanol (2.5 mL) and water (1.5 mL) was stirred at 90° C. overnight under an atmosphere of argon. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=1/1-2/1) to afford the title compound (0.292 g).

Workup

customThe organic layer was separated
washwashed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=1/1-2/1)

Sources & evidence

ORD record: ord-5aa29b14a61e424d89d540f12ed73186
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417169B2

Reaction notes

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