Potassium Carbonate → HCID 86641475, compound

HRID 1047948Notes

Reaction equation

HRID 1047948 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([F:10])[C:4]=1[CH2:11]Br.[N+:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[C-:14].C([O-])([O-])=O.[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH2:19]([O:18][C:16]([C:15]1([N+:13]#[C-:14])[CH2:11][C:4]2[C:3](=[CH:8][CH:7]=[C:6]([F:9])[C:5]=2[F:10])[CH2:2]1)=[O:17])[CH3:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 533707Ethyl isocyanoacetateHCID 59314333HCID 59314333, compound

Product 1

HCID 86641475HCID 86641475, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of compound 1,2-bis-bromomethyl-3,4-difluoro-benzene (8 g, 0.027 mol), ethyl isocyanoacetate (3.01 g, 0.0266 mol), K2CO3 (22.07 g, 0.159 mol) and tetrabutylammonium hydrogen sulphate (5.45 g, 0.016 mol) in ACN (200 ml) is refluxed for overnight. After complete consumption of starting material the reaction mixture is cooled to RT and ACN is removed under reduced pressure. Water (300 mL) is added to the crude mass and then extracted with EtOAc (3×250 mL). The combined organic extracts are washed with water, dried and concentrated to give a crude product. The crude product is purified by column chromatography (silica, 3% EtOAc in hexane) and the solvent removed to give a viscous liquid (1.6 g, 23.7%).

Workup

  1. temperatureis refluxed for overnight
  2. customAfter complete consumption of starting material the reaction mixture
  3. customACN is removed under reduced pressure
  4. additionWater (300 mL) is added to the crude mass
  5. extractionextracted with EtOAc (3×250 mL)
  6. washThe combined organic extracts are washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto give a crude product
  10. customThe crude product is purified by column chromatography (silica, 3% EtOAc in hexane)
  11. customthe solvent removed

Sources & evidence

ORD record
ord-1f163a56015f4ab7b2fbfe9a77fa8658
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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