Ethyl Acetate → HCID 54544988, compound

HRID 1699815Notes

Reaction equation

HRID 1699815 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([Cl:10])[CH:3]=1.[C:11]1(OB(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Cl:10][C:4]1[CH:3]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 54544988HCID 54544988, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a suspension of tetrakis(triphenylphosphine)palladium(O) (16 mg) in toluene (1 ml) was added 4bromo-2-chlorobenzyl alcohol (100 mg) at room temperature, and the mixture was stirred. After 10 min, to the reaction mixture were added a solution of phenylboric acid (83 mg) in ethanol (0.1 ml) and a 2M aqueous sodium carbonate solution (0.9 ml), and the mixture was refluxed under heating. After 1 hr, the reaction mixture was cooled, ethyl acetate was added, and the mixture was filtered through Celite. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated, and the residue was subjected to flash silica gel column chromatography (silica gel, 40 ml, eluent: hexane-ethyl acetate=3-1) to give crude crystals. The crystals were washed with hexane to give the objective compound (76 mg) as colorless crystals.

Workup

  1. temperatureunder heating
  2. waitAfter 1 hr
  3. temperaturethe reaction mixture was cooled
  4. filtrationthe mixture was filtered through Celite
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe filtrate was concentrated
  8. customto give crude crystals
  9. washThe crystals were washed with hexane

Sources & evidence

ORD record
ord-f008b299e1b24e18b2bb0e04f3d56ac0
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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