Potassium Phosphate, Tribasic → HCID 86674213, compound

HRID 2167150Notes

Reaction equation

HRID 2167150 reaction equation
Cl[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:3]=1[CH:4]=[O:5].[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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]>[Cl:14][C:6]1[C:3]([CH:4]=[O:5])=[C:2]([C:22]2[CH:23]=[CH:24][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:20][CH:21]=2)[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343694-Methoxycarbonylphenylboronic acidHCID 147939142,6-Dichloro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 86674213HCID 86674213, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

2,6-Dichloro-4-(trifluoromethyl)benzaldehyde (406 mg, 1.7 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (150 mg, 0.8 mmol), Pd(dppf)Cl2 (81 mg, 0.1 mmol) and K3PO4 (769 mg, 3.3 mmol) were dissolved in wet 1,4-dioxane (20 mL) and the resulting mixture was heated to 90° C. After 10 h the resulting mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-1b16dc9286ea4115b5dcf2eeffa3ee3f
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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