Potassium Carbonate → 1-Bromo-2-(2-benzyloxyeth-1-yloxy)-4-methoxybenzene

HRID 863144Notes

Reaction equation

HRID 863144 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:24][CH2:25][CH2:26]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:26][CH2:25][O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 134938392-Bromo-5-methoxyphenol

Product 1

HCID 184276801-Bromo-2-(2-benzyloxyeth-1-yloxy)-4-methoxybenzeneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-bromo-2-hydroxy-4-methoxy benzene (68.3 g, 0.336 moles), anhydrous potassium carbonate (51.2 g 0.37 moles) and 0.5 L of N,N-dimethylformamide was heated to 65° C. Benzyloxyethylbromide (76.0 g, 0.353 moles) was added dropwise over 0.5 hr. After stirring for 1.5 hr. at 65° C., the reaction mixture was cooled and filtered. The filtrate was diluted with 1 L of deionized water, and extracted with 3×0.5 L ethyl acetate. The organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo. Distillation gave 93 g (83%) of product as a yellow liquid (b.p. 170°-175° C., 0.5 mm).

Workup

  1. temperatureat 65° C., the reaction mixture was cooled
  2. filtrationfiltered
  3. additionThe filtrate was diluted with 1 L of deionized water
  4. extractionextracted with 3×0.5 L ethyl acetate
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. distillationDistillation

Sources & evidence

ORD record
ord-1e82188f4d584930b84806ad8d9a28cb
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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