Methyl Acrylate → Methyl 3-methyl-4-trifluoromethylcinnamate

HRID 2212640Notes

Reaction equation

HRID 2212640 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.[CH3:22][C:23]1[CH:24]=[C:25](Cl)[CH:26]=[CH:27][C:28]=1[C:29]([F:32])([F:31])[F:30].C1(C(N)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CC(N(C)C)=O>[CH3:22][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:28]=1[C:29]([F:30])([F:31])[F:32])[CH:3]=[CH:2][C:1]([O:5][CH3:6])=[O:4]

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 316378Di-tert-butylphenylphosphineHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 127123384-Chloro-2-methyl-1-(trifluoromethyl)benzene

Product 1

HCID 69642322Methyl 3-methyl-4-trifluoromethylcinnamateYield 86%

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. 1.17 g (6 mmol) of 3-methyl-4-trifluoromethylchlorobenzene and 1.53 ml (7.2 mmol) of dicyclohexylmethylamine 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: 86%, two products in a ratio of 99:1 (trans/cis products).

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-9d64549484ee408c94529c667c2bd8de
Source dataset
uspto-grants-2006_09
Patent number
US07102046B2

Reaction notes

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