Potassium Phosphate, Tribasic → Ethyl 4'-fluoro-2-hydroxy-6-propoxybiphenyl-4-carboxylate

HRID 531009Notes

Reaction equation

Br[C:2]1[C:12]([O:13][CH2:14][CH2:15][CH3:16])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:17].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[C:12]([O:13][CH2:14][CH2:15][CH3:16])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[OH:17])=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Palladium acetate (1.11 g) was added to a mixture of ethyl 4-bromo-3-hydroxy-5-propoxybenzoate (30.0 g), tripotassium phosphate (63.0 g), (4-fluorophenyl)boronic acid (34.6 g), and tricyclohexylphosphine (20% toluene solution, 17.6 mL) in toluene (200 mL) and water (100 mL), and the resultant mixture was heated with stirring overnight at 90° C. in an argon atmosphere. The reaction mixture was allowed to cool to room temperature, then diluted with ethyl acetate, and washed with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (31.5 g).

Workup

temperatureto cool to room temperature
washwashed with water and saturated saline in this order
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-7355f96e253443d687a4271c86c6e46b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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