Nitrogen → 3,N,N-Trimethyl-4-vinylbenzamide

HRID 1754903Notes

Reaction equation

HRID 1754903 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:13].[CH:14]([B-](F)(F)F)=[CH2:15].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].N#N>C1COCC1.Cl[Pd]Cl.O>[CH3:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[CH:14]=[CH2:15])[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]

Participants

9

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 189605694-bromo-N,N,3-trimethylbenzamideHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 668162113,N,N-Trimethyl-4-vinylbenzamideYield 90.5%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromo-3,N,N-trimethyl-benzamide (798 mg, 3.30 mmol), potassium vinyltrifluoroborate (579 mg, 4.32 mmol), PdCl2 (59.0 mg, 0.333 mmol), PPh3 (265 mg, 1.01 mmol) and Cs2CO3 (3.22 g, 9.90 mmol) in THF (6.5 ml)-H2O (0.65 ml) was heated with stirring at 85° C. for 21 hours in a sealed test tube in an N2 atmosphere. The reaction mixture was cooled to room temperature and then extracted with ether. The organic layer was washed with water, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 3,N,N-trimethyl-4-vinyl-benzamide (565 mg, 90%).

Workup

  1. temperaturewas heated
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-b0aa6487ebc643aaa7139fa225f38a9b
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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