Water → HCID 23134157, compound

HRID 2220639Notes

Reaction equation

HRID 2220639 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][OH:16])=[CH:11][CH:10]=2)O1.C([C:22]1[C:30]([CH3:31])=[C:29](Br)[CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25])C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O.O1CCO[CH2:44][CH2:43]1>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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(OCC)(=O)C>[OH:16][CH2:15][CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([C:29]2[CH:28]=[CH:27][C:23]([C:24]([O:26][CH2:43][CH3:44])=[O:25])=[CH:22][C:30]=2[CH3:31])=[CH:18][CH:17]=1

Participants

9

Reactant 5

HCID 962WaterHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 231341922-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethan-1-olHCID 23134201HCID 23134201, compound

Product 1

HCID 23134157HCID 23134157, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethanol (0.2 g), ethyl 4-bromo-3-methyl-benzoic acid (0.276 g), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.017 g), [1,1′-bis-(diphenylphosphino)ferrocene] (0.013 g) and tripotassium phosphate (0.643 g) in 1,4-dioxane (5 mL) was stirred at 80° C. overnight under an atmosphere of argon. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to afford the title compound (0.136 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-952056198b3e49ef9e61e7a893782c70
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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