Tetrahydrofuran → 4-(2-Methylpropyl)-3-(trifluoromethyl)benzamide

HRID 423321Notes

Reaction equation

HRID 423321 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[Br-].[CH2:15]([Zn+])[CH:16]([CH3:18])[CH3:17].C1C[O:23]CC1>>[CH3:15][CH:16]([CH3:18])[CH2:17][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[O:23])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 108006474-Bromo-3-(trifluoromethyl)benzonitrileHCID 178448254HCID 178448254, compound

Product 1

HCID 570578624-(2-Methylpropyl)-3-(trifluoromethyl)benzamide

Procedure

To a solution of 4-bromo-3-trifluoromethylbenzonitrile (1.25 g, 5.0 mmol) and isobutylzinc bromide (25 mmol) in THF (50 mL, 25 mmol) under argon was added 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (612 mg, 0.75 mmol) and the reaction heated at reflux for 5 h. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (80 mL) and water (80 mL). A solid formed and was filtered off and discarded. The organic layer was washed with water (80 mL) before it was dried (phase separator) and concentrated in vacuo to give the crude title compound as a black oil. This was used directly in the next step (1.35 g).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate (80 mL) and water (80 mL)
  5. customA solid formed
  6. filtrationwas filtered off
  7. washThe organic layer was washed with water (80 mL) before it
  8. customwas dried (phase separator)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc994e21b9f242e2a9dc24413ccd496b
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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