Triethylamine → 3-Formyl-5-(prop-1-en-2-yl)benzonitrile

HRID 2071088Notes

Reaction equation

HRID 2071088 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH:10]=[O:11])[CH:9]=1)[C:5]#[N:6].B(F)(F)F.[C:16]([K])([CH3:18])=[CH2:17].C(N(CC)CC)C>CC(O)C.O.CCOCC.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]>[CH:10]([C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([C:16]([CH3:18])=[CH2:17])[CH:9]=1)[C:5]#[N:6])=[O:11]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 534255233-Bromo-5-formylbenzonitrileHCID 178456118HCID 178456118, compound

Product 1

HCID 595696913-Formyl-5-(prop-1-en-2-yl)benzonitrile

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

To 3-bromo-5-formylbenzonitrile (420 mg, 2 mmol), isopropenyl potassium trifluoroborate (296 mg, 2 mmol) and triethyl amine (0.42 ml) in 2-propanol and water (20 ml) in 2:1 ratio, PdCl2(dppf) (65 mg, 0.08 mmol) was added and the reaction mixture was refluxed for 5 h. Then the reaction mixture was cooled, diluted with ether, washed with water, brine and dried. Crude residue was column chromatographed (60% ethylacetate: 40% hexane) to yield a white solid of 3-formyl-5-(prop-1-en-2-yl)benzonitrile.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. temperatureThen the reaction mixture was cooled
  3. washwashed with water, brine
  4. customdried
  5. customchromatographed (60% ethylacetate: 40% hexane)

Sources & evidence

ORD record
ord-4c7b8b85db8b437bad19a7e9ccc9bbaa
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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