Triethylamine → (E)-Ethyl 3-(2-amino-5-(trifluoromethyl)phenyl)acrylate

HRID 2098129Notes

Reaction equation

HRID 2098129 reaction equation
Br[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:42]([O:46][CH2:47][CH3:48])(=[O:45])[CH:43]=[CH2:44]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:2]=1/[CH:44]=[CH:43]/[C:42]([O:46][CH2:47][CH3:48])=[O:45]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 938992-Bromo-4-trifluoromethylaniline

Product 1

HCID 86649426(E)-Ethyl 3-(2-amino-5-(trifluoromethyl)phenyl)acrylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 2-bromo-4-(trifluoromethyl)aniline (5 g, 20.83 mmol), triethylamine (4.4 mL, 31.2 mmol) and P(o-tol)3 (2.5 g, 8.33 mmol) in DMF (42 mL, 0.5 M) in a glass pressure tube under nitrogen gas were added ethyl acrylate (2.3 g, 23 mmol) and palladium acetate (940 mg, 4.167 mmol). The tube was sealed and heated to 120° C. for 18 h. The resulting solution was concentrated under vacuum and purified by column chromatography. Retention time(min)=2.532, method [1], MS (ESI) 260.1 (M+H).

Workup

  1. customThe tube was sealed
  2. concentrationThe resulting solution was concentrated under vacuum
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-cfd51b6c046e47929c75ea1b5243d9c3
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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