Potassium Carbonate → 1-(2-Bromo-5-chlorobenzyloxy)-4-(2-methoxyethoxy)benzene

HRID 1360013Notes

Reaction equation

HRID 1360013 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9]Br.C([O-])([O-])=O.[K+].[K+].[CH3:17][O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][O:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH2:19][O:18][CH3:17])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118465052-Bromo-5-chlorobenzyl bromideHCID 133135614-(2-Methoxyethoxy)phenol

Product 1

HCID 669702041-(2-Bromo-5-chlorobenzyloxy)-4-(2-methoxyethoxy)benzeneYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.42 g (5 mmol) of the compound obtained in Step 1 was dissolved in 20 ml of acetonitrile, 1.38 g (10 mmol) of K2CO3 and 0.84 g (5 mmol) of 4-(2-methoxyethoxy)phenol were added thereto, which was refluxed for 15 hours. The reaction mixture was distilled under a reduced pressure to remove the solvent, and 20 ml of ethyl acetate was added thereto. The resulting mixture was washed twice with water, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The concentrate was subjected to column chromatography using 20% ethyl acetate/hexane to obtain 1.76 g (yield 95%) of 1-(2-bromo-5-chlorobenzyloxy)-4-(2-methoxyethoxy)benzene.

Workup

  1. temperaturewhich was refluxed for 15 hours
  2. distillationThe reaction mixture was distilled under a reduced pressure
  3. customto remove the solvent, and 20 ml of ethyl acetate
  4. additionwas added
  5. washThe resulting mixture was washed twice with water
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-4f723d9e911b4eb681e8df8a5aaebf65
Source dataset
uspto-grants-2011_02
Patent number
US07879835B2

Reaction notes

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