Potassium Carbonate → 1-(2-Fluoro-4'-hydroxy-biphenyl-4-yl)-cyclopropanecarboxylic acid

HRID 492280

Reaction equation

HRID 492280 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17]([OH:19])=[O:18])[CH2:16][CH2:15]2)=[CH:10][C:9]=1[F:20].OOB([C:25]1[CH:30]=[CH:29]C=[CH:27][CH:26]=1)O>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:20][C:9]1[CH:10]=[C:11]([C:14]2([C:17]([OH:19])=[O:18])[CH2:16][CH2:15]2)[CH:12]=[CH:13][C:8]=1[C:25]1[CH:30]=[CH:29][C:1]([OH:4])=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 116518041-(4-Bromo-3-fluorophenyl)cyclopropane-1-carboxylic acidHCID 58822967Hydroxyl phenylboronic acid acid

Product 1

HCID 116014911-(2-Fluoro-4'-hydroxy-biphenyl-4-yl)-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of K2CO3 (447 mg, 3.2 mmoles) in dioxane (30 ml) and water (3 ml), 250 mg of 1-(4-bromo-3-fluoro-phenyl)-cyclopropanecarboxylic acid (1.0 mmole) and 265 mg of hydroxyphenylboronic acid (1.9 mmoles) are added under stirring. Under nitrogen atmosphere, 39 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (PdCl2-DPPF) are added. The resulting mixture is heated at 65° C. for one hour, then the reaction is quenched by adding a 10% w/v HCl solution.

Workup

  1. customthe reaction is quenched
  2. additionby adding a 10% w/v HCl solution

Sources & evidence

ORD record
ord-f2a4d599fe144044bbecca06e5396d45
Source dataset
uspto-grants-2009_05
Patent number
US07531692B2

Linked notes

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