Hydrochloric Acid → HCID 22619377, compound

HRID 1031511Notes

Reaction equation

HRID 1031511 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[CH:12]=[CH2:13].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[C:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:12](=[CH2:13])[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:3][CH:4]=1)#[N:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15458tert-Butyl acrylateHCID 27914Benzeneacetonitrile, 4-bromo-HCID 80271Tri-o-tolylphosphine

Product 1

HCID 22619377HCID 22619377, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

p-Bromophenylacetonitrile (50 g), t-butyl acrylate (46 ml), palladium (II) acetate (575 mg) and tri-o-tolylphosphine (3.1 g) are combined with 125 ml triethylamine in a steel pressure reactor and heated at 140° for 16 hours. The reaction mixture is cooled to room temperature and poured into 500 ml 3N hydrochloric acid at 0°. The solids are extracted into ethyl acetate and the ethyl acetate solution is extracted with saturated NaCl solution and dried over magnesium sulfate. The crude product is triturated with ether:hexane (1:1), filtered and dried under vacuum to yield t-butyl p-(cyanomethyl)-phenylacrylate; m.p. 80°-82°; NMR (CDCl3): 7.5 (2H,d), 7.32 (2H,d), 6.39 (2H,d), 3.78 (2H,s), 1.52 (9H,s).

Workup

  1. temperatureheated at 140° for 16 hours
  2. extractionThe solids are extracted into ethyl acetate
  3. extractionthe ethyl acetate solution is extracted with saturated NaCl solution
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product is triturated with ether:hexane (1:1)
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-2ae4ffa2688242759240bf5939e228f9
Source dataset
uspto-grants-1990_09
Patent number
US04954504

Reaction notes

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