Water → HCID 54544988, compound

HRID 1699814Notes

Reaction equation

HRID 1699814 reaction equation
[Cl-].[Li+].Br[C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[C:6]([Cl:12])[CH:5]=1.[C:13]1([Sn](CCCC)(CCCC)CCCC)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>O1CCOCC1.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:12][C:6]1[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][C:7]=1[CH2:8][OH:9]

Participants

7

Reactant 4

HCID 962WaterHCID 433294Lithium ChlorideHCID 607632TributylphenyltinHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 54544988HCID 54544988, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of lithium chloride (482 mg) in anhydrous 1,4-dioxane (12 ml) were added 4-bromo-2-chlorobenzyl alcohol (1.05 g), phenyl tributyl tin (1.74 g) and tetrakis(triphenylphosphine)palladium(O) (110 mg) under a nitrogen atmosphere, and the mixture was refluxed under heating. After 5 hr, the reaction mixture was cooled and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and 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, 50 ml, eluent: hexane-ethyl acetate=2-1). The eluate was washed with hexane to give the objective compound (220 mg) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating
  3. temperaturethe reaction mixture was cooled
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe filtrate was concentrated
  8. washThe eluate was washed with hexane

Sources & evidence

ORD record
ord-19d67b224b2748298f959b197ace1563
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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