Ethyl bromoacetate → HCID 43423278, compound

HRID 898481Notes

Reaction equation

HRID 898481 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH:2]=[CH2:3].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH:2]=[CH2:3])[CH3:17]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 156242-Allylphenol

Product 1

HCID 43423278HCID 43423278, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-allyl-phenol (10 g, 74.5 mmol), ethyl 2-bromoacetate (12.4 mL, 112 mmol) and cesium carbonate (36.5 g, 112 mmol) in DMF (180 mL) was heated at 60° C. overnight. The mixture was cooled and filtered through a pad of celite. The filtrate was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by column chromatography on silica gel to give 14.5 g of title compound. 1H NMR (400 MHz, CDCl3) • 7.19˜7.14 (m, 2H), 6.97˜6.92 (m, 1H), 6.73 (d, J=8.1 Hz, 1H), 6.09˜5.95 (m, 1H), 5.11˜5.02 (m, 2H), 4.54 (s, 2H), 4.26 (q, J=7.2 Hz, 2H), 3.46 (d, J=6.8 Hz, 2H), 1.29 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through a pad of celite
  3. additionThe filtrate was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8e58cb3a80ee4e6eade6fe9b3b8c14b6
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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