Ethyl Acetate → HCID 86685062, compound

HRID 532179Notes

Reaction equation

HRID 532179 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[Cl:12].[F:13][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2.CC(=O)OCC>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH2:10][F:13])=[CH2:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[Cl:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724933SelectfluorHCID 86685061HCID 86685061, compound

Product 1

HCID 86685062HCID 86685062, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 1,2,3-trichloro-5-(prop-1-en-2-yl)benzene (660 mg, 3 mmol) and 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium bis(tetrafluoroborate) (1.115 g, 3.15 mmol) in DMF (25 ml). The mixture was stirred at 75° C. for 3 h. The mixture was washed with H2O and extracted with EA (30 ml×2). The mixture was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (7:1 to 5:1) to give the desired product (260 mg, yield 36%).

Workup

  1. washThe mixture was washed with H2O
  2. extractionextracted with EA (30 ml×2)
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography over silica gel
  5. washeluted with PE

Sources & evidence

ORD record
ord-a203d74c49cc4872a04613c2c74fcbdf
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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