Ethyl Acetate → HCID 90422687, compound

HRID 1050181Notes

Reaction equation

HRID 1050181 reaction equation
[F:1][C:2]([F:22])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(=O)OCC>CO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:2]([F:1])([F:22])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:10]([C:18]([F:19])([F:20])[F:21])[CH:11]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 90423135HCID 90423135, compound

Product 1

HCID 90422687HCID 90422687, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of ethyl 2,2-difluoro-3-(4-nitro-2-(trifluoromethyl)phenyl)propanoate (220 mg, 0.672 mmol) in MeOH (10 mL) was added Pd/C (71.6 mg, 0.672 mmol) under N2. The mixture was then stirred under a H2 atmosphere for 1 h. LCMS and TLC (PE/EA=5:1, Rf=0.3) showed the reaction was finished. The mixture was filtered and the filtrate was concentrated to give ethyl 3-(4-amino-2-(trifluoromethyl)phenyl)-2,2-difluoropropanoate (190 mg, 0.573 mmol, 85% yield): NMR (400 MHz, CD3OD-d4) δ 7.15 (s, 1H), 6.97 (d, J=2.2 Hz, 1H), 6.81 (dd, J=2.1, 8.4 Hz, 1H), 4.24 (q, J=7.1 Hz, 2H), 3.42 (t, J=16.8 Hz, 2H), 1.24 (t, J=7.1 Hz, 3H). ES-LCMS m/z 298 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f946f7af753940dfa4a43662ec1c7728
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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