Trifluoroacetic acid → {3-[(3-Chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid

HRID 1874779Notes

Reaction equation

HRID 1874779 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:35])=[C:13]([CH:20](C(OC(C)(C)C)=O)[C:21]([O:23]C(C)(C)C)=[O:22])[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:35])=[C:13]([CH2:20][C:21]([OH:23])=[O:22])[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59451518Bis(1,1-dimethylethyl) {3-[(3-chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}propanedioate

Product 1

HCID 59451579{3-[(3-Chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude bis(1,1-dimethylethyl) {3-[(3-chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}propanedioate was dissolved in CH2Cl2 (25 mL) and TFA (25 mL) and heated to reflux for 2 h. The reaction mixture was cooled to RT and evaporated. Water (50 mL) and EtOAc (50 mL) were added, the layers were separated and the aqueous layer extracted with EtOAc (3×50 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated to give the title compound as an oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.03 (d, 1H), 7.81 (s, 1H), 7.50-7.62 (m, 3H), 3.84 (s, 2H). MS: m/z 349.1 (M−1).

Workup

  1. temperatureto reflux for 2 h
  2. customevaporated
  3. additionWater (50 mL) and EtOAc (50 mL) were added
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted with EtOAc (3×50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-2b62d439700040a296ab256f8ebf4f5c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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