Ethyl bromoacetate → HCID 66837481, compound

HRID 1993904Notes

Reaction equation

HRID 1993904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(#N)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:9])[CH:4]=1)[CH3:22]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 27245234-Chloro-3-fluorophenol

Product 1

HCID 66837481HCID 66837481, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-3-fluoro-phenol (0.50 g, 3.34 mmol) in acetonitrile (8 ml) were added caesium carbonate (1.31 g, 4.01 mmol) and ethyl bromoacetate (0.40 ml, 3.51 mmol). The resulting suspension was stirred at room temperature for 1 hour and was then poured onto ice/aq. ammonium chloride solution (50 ml) and the resulting mixture was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=gradient 100:0-70:30) to yield a colourless oil (0.81 g, 100%); 1H NMR (300 MHz, CDCl3): 7.30 (1H, d), 6.73 (1H, dd), 6.66 (1H, dd), 4.59 (2H, s), 4.28 (2H, q), 1.30 (3H, t).

Workup

  1. additionwas then poured onto ice/aq
  2. extractionammonium chloride solution (50 ml) and the resulting mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=gradient 100:0-70:30)

Sources & evidence

ORD record
ord-d1ac471393f84c53834d7f9e0a706024
Source dataset
uspto-grants-2010_01
Patent number
US07652055B2

Reaction notes

Loading…