Potassium Carbonate → 1-Bromo-3-(2-methoxyethoxy)benzene

HRID 341162Notes

Reaction equation

HRID 341162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][O:10][CH2:11][CH2:12]Br.C([O-])([O-])=O.[K+].[K+]>CO.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:12][CH2:11][O:10][CH3:9])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 809722-Bromoethyl methyl ether

Product 1

HCID 183796081-Bromo-3-(2-methoxyethoxy)benzeneYield 69.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-bromophenol (0.865 g, 5 mmol) in MeOH (1.5 ml) was added 2-bromoethyl methyl ether (0.56 ml, 6 mmol) followed by K2CO3 (0.68 g, 5 mmol). The mixture was heated using microwave irradiation in a CEM discover microwave synthesizer (50 W) at 100° C. until the reaction was complete. The reaction was diluted with ether and filtered to remove solid which was washed with further ether. Filtrate concentrated under reduced pressure to give (0.8 g) of product.

Workup

  1. temperatureThe mixture was heated
  2. custommicrowave irradiation in a CEM
  3. customat 100° C.
  4. filtrationfiltered
  5. customto remove solid which
  6. washwas washed with further ether
  7. concentrationFiltrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7528f84df88e4063aaa16b9f7cb1b479
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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