Hydrochloric Acid → (2E)-3-(4-Cyanophenyl)-2-propenoic acid

HRID 747741Notes

Reaction equation

HRID 747741 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CCCC)CCCC)CCC.Cl>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2](/[CH:12]=[CH:11]/[C:10]([OH:14])=[O:13])=[CH:3][CH:4]=1)#[N:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 7622TributylamineHCID 12162Benzonitrile, 4-bromo-HCID 80271Tri-o-tolylphosphine

Product 1

HCID 735786(2E)-3-(4-Cyanophenyl)-2-propenoic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

3.64 g (20 mmol) of 4-bromobenzonitrile and 2.88 g (40 mmol) of acrylic acid were dissolved in 40 ml of acetonitrile. 49 mg (0.2 mmol) of palladium (II) acetate, 365 mg (1.2 mmol) of tri-o-tolylphosphine and 7.41 g (40 mmol) of tributylamine were added to the solution, and they were heated under reflux overnight. The reaction liquid was poured into 4 N aqueous hydrogen chloride solution. The precipitates thus formed were taken by the filtration, washed with 4 N aqueous hydrogen chloride solution, water and ethyl acetate, and then dried in vacuo to obtain the title compound.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux overnight
  3. customThe reaction liquid
  4. customThe precipitates thus
  5. customformed
  6. filtrationwere taken by the filtration
  7. washwashed with 4 N aqueous hydrogen chloride solution, water and ethyl acetate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-92086e604333490d9ca7c9bfd6e0b339
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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