3-Chlorobenzotrifluoride → HCID 6190431, compound

HRID 2212642Notes

Reaction equation

HRID 2212642 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C(C)(C)C)C(C)(C)C)C=CC=CC=1.Cl[C:25]1[CH:26]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:29][CH:30]=1.C1(C(N)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CC(N(C)C)=O>[F:32][C:31]([F:34])([F:33])[C:27]1[CH:26]=[C:25](/[CH:1]=[CH:2]/[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 73743-ChlorobenzotrifluorideHCID 7501StyreneHCID 316378Di-tert-butylphenylphosphineHCID 10774245alpha-Cyclohexylcyclohexanemethanamine

Product 1

HCID 6190431HCID 6190431, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

0.745 g (7.2 mmol) of styrene, 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. 1.08 g (6 mmol) of 3-chlorobenzotrifluoride 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: 1.43 g (96% 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-c1fd83eb8b9f4ab6a3b234aad9580f6e
Source dataset
uspto-grants-2006_09
Patent number
US07102046B2

Reaction notes

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