N,N-Dimethylglycine → 1-Bromo-4-(4-methylphenoxy)benzene

HRID 2035924Notes

Reaction equation

HRID 2035924 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)CC(O)=O>CN(C=O)C.[NH4+].[Cl-].[Cu]I>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 2879P-CresolHCID 78041,4-DibromobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 221862981-Bromo-4-(4-methylphenoxy)benzeneYield 65%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-methylphenol (30.0 g), 1,4-dibromobenzene (54.5 g), copper(I) iodide (4.40 g), potassium carbonate (5.11 g) and N,N-dimethylglycine (2.86 g) in DMF (300 ml) was stirred at 100° C. under N2 for 18 hr. The mixture was diluted with sat. NH4Cl aq. at 0° C. and extracted with EtOAc. The organic layer was separated, washed with sat. NH4Cl aq., 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with hexane) to give the title compound (39.5 g) as a colorless solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with sat. NH4Cl aq., 1N NaOH aq. and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, eluted with hexane)

Sources & evidence

ORD record
ord-f2efbd6029dc43cb97c84a31cd7d4685
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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