Water → HCID 69673054, compound

HRID 1751388Notes

Reaction equation

HRID 1751388 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[CH2:18][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 118465052-Bromo-5-chlorobenzyl bromide

Product 1

HCID 69673054HCID 69673054, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methoxyphenol (0.84 mL, 7.3 mmol) and 1-bromo-2-(bromomethyl)-4-chlorobenzene (2 g, 7 mmol) in DMF (70 mL) was added potassium carbonate (1.94 g, 14 mmol). The reaction mixture was stirred at room temperature for 16 hours, then poured into water (500 mL) extracted into ethyl acetate. The organics were washed with water and brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography to yield 1-bromo-4-chloro-2-((3-methoxyphenoxy)methyl)benzene (2 g, 87%)

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organics were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d4949a7e019b48f787ad2e78c13d13ae
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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