Water → HCID 86674207, compound

HRID 2167130Notes

Reaction equation

HRID 2167130 reaction equation
Br[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(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]>[CH:4]([C:3]1[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[C:21]1[CH:22]=[CH:23][C:18]([C:16]([O:15][CH3:14])=[O:17])=[CH:19][CH:20]=1)=[O:5]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 30203732-Bromo-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 86674207HCID 86674207, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-bromo-4-(trifluoromethyl)benzaldehyde (1.0 g, 4.0 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (854 mg, 4.7 mmol), Pd(dppf)Cl2 (324 mg, 0.4 mmol), and K2CO3 (1.1 g, 7.9 mmol) were dissolved in 1,4-dioxane (24 mL) and water (6 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Sources & evidence

ORD record
ord-9d0a2c3ad5a040b6b22607d816423936
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

Loading…