Benzeneacetonitrile, 4-bromo- → Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 1617233Notes

Reaction equation

HRID 1617233 reaction equation
[OH:1][CH:2]([CH3:9])[C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].Br[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1.C([O-])(O)=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CCOCC>[C:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:8][CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:12][CH:13]=1)#[N:19]

Participants

7

Reactant 3

HCID 27914Benzeneacetonitrile, 4-bromo-HCID 516892Sodium BicarbonateHCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

Product 1

HCID 59590640Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (19.5 g), 2-(4-bromophenyl)acetonitrile (40 g), PdOAc2 (2 g), tetrabutylammonium bromide (40 g) and NaHCO3 (31.5 g) in THF (300 ml) was heated under N2 at reflux for 24 h. The mixture was cooled, diluted with ether (500 ml) and filtered through celite. The filtrate was washed with water, dried and evaporated under reduced pressure to give an oil, used crude in next step.

Workup

  1. temperaturewas heated under N2
  2. temperatureat reflux for 24 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customto give an oil

Sources & evidence

ORD record
ord-3d1bb5fd6f774048b1261d62463f46ae
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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