Ethyl Acrylate → HCID 86649425, compound

HRID 2098107Notes

Reaction equation

HRID 2098107 reaction equation
Br[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([F:13])=[CH:5][C:3]=1[NH2:4].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:36]([O:40][CH2:41][CH3:42])(=[O:39])[CH:37]=[CH2:38]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:4][C:3]1[CH:5]=[C:6]([F:13])[C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:2]=1/[CH:38]=[CH:37]/[C:36]([O:40][CH2:41][CH3:42])=[O:39]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 687591875-Fluoro-2-iodo-4-trifluoromethyl-phenylamine

Product 1

HCID 86649425HCID 86649425, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
85 °C

Procedure

2-Bromo-5-fluoro-4-(trifluoromethyl)aniline (0.97 mmol) and P(o-tol)3 (0.40 mmol) were dissolved in triethylamine (2.0 mL) in a glass pressure tube and nitrogen gas was bubbled through the solution via a gas dispersion tube for 10 minutes. Ethyl acrylate (1.0 mmol) and palladium acetate (0.20 mmol) were added to the reaction mixture and the tube was sealed and placed into an oil bath pre-heated to 85° C. for 18 h. The resulting solution was concentrated under vacuum and purified via an isco column. Retention time (min)=2.504, method [1], MS (ESI) 278.0 (M+H).

Workup

  1. customnitrogen gas was bubbled through the solution via a gas dispersion tube for 10 minutes
  2. customthe tube was sealed
  3. customplaced into an oil bath
  4. concentrationThe resulting solution was concentrated under vacuum
  5. custompurified via an isco column

Sources & evidence

ORD record
ord-a308a17fabc04b1f90663cbd83492762
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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