Potassium Carbonate → HCID 22633322, compound

HRID 2417382Notes

Reaction equation

HRID 2417382 reaction equation
C([O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][C:8]([CH:9]=[O:10])=[C:7](Br)[CH:6]=1)(=O)C.[CH:16]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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]>[OH:4][C:5]1[CH:6]=[C:7]([C:22]2[CH:23]=[CH:24][C:19]([CH:16]([CH3:18])[CH3:17])=[CH:20][CH:21]=2)[C:8]([CH:9]=[O:10])=[CH:11][C:12]=1[O:13][CH3:14]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2623485-Bromo-4-formyl-2-methoxyphenyl acetateHCID 27734804-Isopropylphenylboronic acid

Product 1

HCID 22633322HCID 22633322, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (273 mg, 1 mmol) of 4-Acetoxy-2-bromo-5-methoxybenzaldehyde, (164 mg, 1 mmol) of 4-isopropylphenylboronic acid and 276 mg (2 mmol) of K2CO3 in 5 mL of DMF and 1 mL of H2O was added 73.1 mg (0.1 mmol) of Pd(dppf)Cl2. The mixture was heated at 80° C. overnight. After the removal of the catalyst via filtration, the mixture was repartitioned between EtOAc and H2O. Aqueous layer was extracted 3 times with EtOAc and organic layers were combined and dried over Na2SO4. After the removal of the solvent, the residue was chromatographed to give 362 mg of 5-Hydroxy-4′-isopropyl-4-methoxy-biphenyl-2-carbaldehyde (72%).

Workup

  1. customAfter the removal of the catalyst
  2. filtrationvia filtration
  3. extractionAqueous layer was extracted 3 times with EtOAc and organic layers
  4. dry with materialdried over Na2SO4
  5. customAfter the removal of the solvent
  6. customthe residue was chromatographed

Sources & evidence

ORD record
ord-9b402a2cfb4446f29d5c24932703bd13
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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