2-Bromophenol → HCID 11042902, compound

HRID 567881Notes

Reaction equation

HRID 567881 reaction equation
BrC1C=CC=CC=1O.C[C:10]1[C:15]2O[C:17]3[C:25]([OH:26])=[C:24]([OH:27])[CH:23]=[C:22]([OH:28])[C:18]=3[C:19](=[O:21])[CH2:20][C:14]=2[CH:13]=[CH:12][CH:11]=1>C1(C)CCC(C(C)C)C(N(C2C(C(C)C)CCC(C)C2)C=O)C1.CCOCC.[OH-].[Na+].CCCCCC.[Cu].[Cu](I)I.C(=O)([O-])[O-].[K+].[K+]>[OH:27][C:24]1[C:25]([OH:26])=[CH:17][C:18]2[C:19](=[O:21])[CH2:20][C:14]3[CH:15]=[CH:10][CH:11]=[CH:12][C:13]=3[O:28][C:22]=2[CH:23]=1

Participants

10

Reactant 2

HCID 72442-BromophenolHCID 15512488HCID 15512488, compound2×

Product 1

HCID 11042902HCID 11042902, compoundYield 298.3%

Reagents, catalysts & solvents 7

HCID 11430Potassium CarbonateCatalystHCID 23978CopperCatalystHCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolventHCID 14798Sodium HydroxideSolventHCID 21263165HCID 21263165, compoundSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromophenol (380 mg) in N,N-dimenthylformamide (2.5 ml) were added potassium carbonate (15 mg), copper (19.5 mg), copper iodide, (15 mg) and 6-bromo-3,4-dimethoxyacetophenone (Compound 4) (130 mg) and the mixture was stirred at 100° C. for four hours. The reaction mixture was diluted with ether and 5% aqueous solution of sodium hydroxide was added thereto followed by stirring for five minutes. This was diluted with a mixture of ether and hexane and was washed with 5% aqueous solution of sodium hydroxide, water and saturated sodium chloride solution successively. The organic layer was collected and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom. The resulting residue was purified by a silica gel chromatography (hexane:ether=3:1) to give the title compound (345 mg, 80%) as yellow oil.

Workup

  1. additionwas added
  2. stirringby stirring for five minutes
  3. washwas washed with 5% aqueous solution of sodium hydroxide, water and saturated sodium chloride solution successively
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe resulting residue was purified by a silica gel chromatography (hexane:ether=3:1)

Sources & evidence

ORD record
ord-c480b0e068f8422a9865f95bb8c57bdc
Source dataset
uspto-grants-2001_01
Patent number
US06180659B2

Reaction notes

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