Ethanol → HCID 86727069, compound

HRID 1502019Notes

Reaction equation

HRID 1502019 reaction equation
Br[C:2]1[C:3]([O:11][CH3:12])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:13](O)[CH3:14]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:13]([C:2]1[C:3]([O:11][CH3:12])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[C:5]#[N:6])=[CH2:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 712707103-Bromo-6-fluoro-2-methoxybenzonitrile

Product 1

HCID 86727069HCID 86727069, compound

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

3-bromo-6-fluoro-2-methoxybenzonitrile (4.40 g, 19.1 mmol), potassium vinyl trifluoroborate (5.12 g, 38.3 mmol), PdCl2(dppf)-CH2Cl2 Adduct (0.7 g, 1 mmol) and TEA (5.33 mL, 38.3 mmol) were added to 80 mL ethanol in a 200 mL flask. The reaction mixture was degassed and heated to reflux for 4 h. The reaction mixture was cooled and then most of the ETOH was removed. The residue was diluted with ethyl acetate. The mixture was washed with brine twice. The organic layer was separated and dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified thru a 330 g RediSep column and eluted with 10% ETOAc/hexane solvent system to yield the title compound.

Workup

  1. customThe reaction mixture was degassed
  2. temperatureheated
  3. temperatureto reflux for 4 h
  4. temperatureThe reaction mixture was cooled
  5. custommost of the ETOH was removed
  6. additionThe residue was diluted with ethyl acetate
  7. washThe mixture was washed with brine twice
  8. customThe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated to dryness
  12. customThe residue was purified thru a 330 g RediSep column
  13. washeluted with 10% ETOAc/hexane solvent system

Sources & evidence

ORD record
ord-a8d12e80008641659734bc3e35d009c7
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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