Allyl bromide → 2-(4-Allyloxyphenyl)-proprionic acid methyl ester

HRID 218235Notes

Reaction equation

HRID 218235 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:5].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:22][CH:21]=[CH2:20])=[CH:8][CH:7]=1)[CH3:5]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12549710Methyl 2-(4-hydroxyphenyl)propanoate

Product 1

HCID 685415412-(4-Allyloxyphenyl)-proprionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the product of Example 46A (2.6 g, 12 mmol) in anhydrous dimethylformamide (20 mL) was treated with potassium carbonate (3.3 g, 24 mmol) and allyl bromide (1.2 mL, 13 mmol), and reaction heated for 16 hours at 80° C. Reaction mixture cooled and diluted with ethyl acetate. Mixture washed with water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. Residue purified by normal phase HPLC on silica gel eluting with 3% ethyl acetate/hexane to provide the title compound.

Workup

  1. customReaction mixture
  2. temperaturecooled
  3. washMixture washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customResidue purified by normal phase HPLC on silica gel eluting with 3% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a5c63b169b424b17b57bed2185b62ca9
Source dataset
uspto-grants-2012_06
Patent number
US08198331B2

Reaction notes

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