Potassium Carbonate → Ethyl 2-(4-(benzyloxy)-3-bromophenyl)acetate

HRID 930857Notes

Reaction equation

HRID 930857 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][C:2]=1[Br:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18620106Ethyl 2-(3-bromo-4-hydroxyphenyl)acetate

Product 1

HCID 18620085Ethyl 2-(4-(benzyloxy)-3-bromophenyl)acetateYield 164%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 35a (2.011 mL, 16.90 mmol), and potassium carbonate (5.84 g, 42.3 mmol) in ethanol (100 mL) was refluxed for 2 hours, cooled, concentrated and the residue was partitioned with ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by chromatography (silica gel, 0-20% ethyl acetate in hexane) afforded the title compound (4.84 g, 98%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customthe residue was partitioned with ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by chromatography (silica gel, 0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-622090d298654b53a3358ff02ea7bc9b
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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