Trifluoroacetic acid → [2-Fluoro-3-(1-naphthalenyloxy)-4-nitrophenyl]acetic acid

HRID 1875044Notes

Reaction equation

HRID 1875044 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:14]([O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[C:13]([N+:26]([O-:28])=[O:27])[CH:12]=[CH:11][C:10]=1[CH:29](C(OC(C)(C)C)=O)[C:30]([O:32]C(C)(C)C)=[O:31]>ClCCl.C(OCC)(=O)C.O>[F:8][C:9]1[C:14]([O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[C:13]([N+:26]([O-:28])=[O:27])[CH:12]=[CH:11][C:10]=1[CH2:29][C:30]([OH:32])=[O:31]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68483921Bis(1,1-dimethylethyl) [2-fluoro-3-(1-naphthalenyloxy)-4-nitrophenyl]propanedioate

Product 1

HCID 68487359[2-Fluoro-3-(1-naphthalenyloxy)-4-nitrophenyl]acetic acidYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Trifluoroacetic acid (30 mL, 389 mmol) was added to a solution of bis(1,1-dimethylethyl) [2-fluoro-3-(1-naphthalenyloxy)-4-nitrophenyl]propanedioate (22.89, g, 46 mmol) in dichloromethane (250 mL). the mixture was heated under a reflux condenser at 45° C. for 4 hrs. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated to give the title compound (15.70 g, 100%). 1H NMR (400 MHz, chloroform-d) δ ppm 8.91 (br. s., 1H), 8.30-8.44 (m, 1H), 7.82-7.91 (m, 2 H), 7.51-7.62 (m, 3H), 7.21-7.35 (m, 2H), 6.58 (d, 1H), 3.82 (d, 2H). ES MS: m/z 340 (M−1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4c05d247a9564c3fa8f9613e4e84b9ad
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…