Methyl Acrylate → HCID 69642708, compound

HRID 2212639Notes

Reaction equation

HRID 2212639 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C1(P(C(C)(C)C)C(C)(C)C)C=CC=CC=1.[C:22]([C:24]1[CH:25]=[C:26](Cl)[CH:27]=[CH:28][C:29]=1[C:30]([F:33])([F:32])[F:31])#[N:23].C1(C(N)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CC(N(C)C)=O>[C:22]([C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][C:29]=1[C:30]([F:31])([F:32])[F:33])[CH:3]=[CH:2][C:1]([O:5][CH3:6])=[O:4])#[N:23]

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 316378Di-tert-butylphenylphosphineHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 177508345-Chloro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 69642708HCID 69642708, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

0.619 g (7.2 mmol) of methyl acrylate, 38.7 mg (120 μmol) of NBu4Br, 6.7 mg (30 μmol) of palladium acetate and 26.7 mg (120 μmol) of phenyldi(t-butyl)phosphine are weighed into a Schlenk vessel. 1.23 g (6 mmol) of 3-cyano-4-trifluoromethylchlorobenzene and 1.53 ml (7.2 mmol) of dicylohexylmethylamine and also 3.5 ml of dimethylacetamide are then added. The Schlenk vessel is placed in a heating bath at 130° C. and the contents are stirred. After 4 hours, the contents are poured into 30 ml of water and the product is extracted by shaking with t-butyl methyl ether. After drying the organic phase over MgSO4, the solvent is removed under reduced pressure and the product is isolated. Yellowish, crystalline solid, yield: 1.31 g (85.5% of theory).

Workup

  1. customThe Schlenk vessel is placed in a heating bath at 130° C.
  2. extractionthe product is extracted
  3. stirringby shaking with t-butyl methyl ether
  4. dry with materialAfter drying the organic phase over MgSO4
  5. customthe solvent is removed under reduced pressure
  6. customthe product is isolated

Sources & evidence

ORD record
ord-d3ea19cf326f436da6b17e7329bd3c82
Source dataset
uspto-grants-2006_09
Patent number
US07102046B2

Reaction notes

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