Ethyl bromoacetate → HCID 69871087, compound

HRID 398150Notes

Reaction equation

HRID 398150 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:30]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 22633496HCID 22633496, compound

Product 1

HCID 69871087HCID 69871087, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

4-Benzyloxy-2-phenethylphenol (1,77 mmol) was dissolved in anhydrous DMF (4 mL), followed by the addition of ethyl bromoacetate (0.29 mL, 2.65 mmol), and cesium carbonate (0.75 g, 2.30 mmol). The mixture was then heated for 18 h (55° C.). The reaction mixture was then cooled and concentrated in vacuo. The crude residue was partitioned between ethyl acetate (70 mL) and water (40 mL). The organic layer was washed with brine, dried (Na2SO4), and removed in vacuo to give the desired product.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was partitioned between ethyl acetate (70 mL) and water (40 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-56616f51ec4a43eeadac43795e94a8b3
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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