Trifluoroacetic acid → HCID 68488923, compound

HRID 1875054Notes

Reaction equation

HRID 1875054 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([N+:22]([O-:24])=[O:23])[CH:12]=[CH:11][C:10]=1[CH:25](C(OC(C)(C)C)=O)[C:26]([O:28]C(C)(C)C)=[O:27]>ClCCl.C(OCC)(=O)C.O>[F:8][C:9]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([N+:22]([O-:24])=[O:23])[CH:12]=[CH:11][C:10]=1[CH2:25][C:26]([OH:28])=[O:27]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68488235HCID 68488235, compound

Product 1

HCID 68488923HCID 68488923, compoundYield 110.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Trifluoroacetic acid (3 mL, 38.9 mmol) was added to a solution of bis(1,1-dimethylethyl) [2-fluoro-4-nitro-3-(phenyloxy)phenyl]propanedioate (2.210 g, 4.94 mmol) in dichloromethane (20 mL). The mixture was heated at 45° C. overnight. The reaction mixture was diluted with ethyl acetate and water. The organic layer was dried over sodium sulfate and the solvent was evaporated to give the crude product (1.59 g, 89% yield) as a gummy solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.70-7.80 (m, 1H), 7.20-7.33 (m, 3H), 7.07 (t, 1H), 6.89 (d, 2H), 3.78 (s, 2H).

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-80fa3bbc75bf4384b1e849c459eab938
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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