Cesium carbonate → 2-(2,4-Dimethylbenzyloxy)ethyl methyl ether

HRID 642967

Reaction equation

HRID 642967 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9].[O:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCC.O>[CH3:15][O:10][CH2:11][CH2:12][O:13][CH2:14][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 68503Benzene, 1-bromo-2,4-dimethyl-HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 592597232-(2,4-Dimethylbenzyloxy)ethyl methyl etherYield 71%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-bromo-m-xylene (30 mg, 0.16 mmol, containing 2-bromo-m-xylene) and 1,4-dioxane (2 ml) were added water (0.2 ml), cesium carbonate (0.16 mg, 0.49 mmol), potassium (2-methoxyethoxymethyl) trifluoroborate (64 mg 0.32 mmol), palladium (II) acetate (3.6 mg, 0.016 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (13 mg, 0.032 mmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 12 hours. After the reaction mixture was allowed to cool at room temperature, to the reaction mixture was added water and hexane. The organic layer was washed with an aqueous saturated sodium chloride solution, and the organic layer was separated. After the organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by thin layer chromatography (hexane 100%) to obtain the title compound (32 mg, 0.16 mmol, 71%) as a mixture of 2-(2,6-dimethylbenzyloxy)ethyl methyl ether derived from 2-bromo-m-xylene contained in a raw material.

Workup

  1. temperatureto cool at room temperature, to the reaction mixture
  2. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  3. customthe organic layer was separated
  4. dry with materialAfter the organic layer was dried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by thin layer chromatography (hexane 100%)

Sources & evidence

ORD record
ord-21d7ff43536e477b95a03f0b14605fdf
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Linked notes

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