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

HRID 1874933Notes

Reaction equation

HRID 1874933 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:34])=[C:12]([CH:19](C(OC(C)(C)C)=O)[C:20]([O:22]C(C)(C)C)=[O:21])[CH:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:11]([F:34])=[C:12]([CH2:19][C:20]([OH:22])=[O:21])[CH:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68487247Bis(1,1-dimethylethyl) {3-[(3-bromo-5-chlorophenyl)oxy]-2-fluoro-4-nitrophenyl}propanedioate

Product 1

HCID 68488957{3-[(3-Bromo-5-chlorophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude bis(1,1-dimethylethyl) {3-[(3-bromo-5-chlorophenyl)oxy]-2-fluoro-4-nitrophenyl}propanedioate was dissolved in CH2Cl2 (100 mL) and TFA (50 mL) and heated to 40° C. for 3 h. The reaction mixture was cooled to RT and concentrated. Water (200 mL) and EtOAc (100 mL) were added, the layers were separated and the aqueous layer extracted with EtOAc (2×100 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 12.17 (br s, 1H), 8.01 (dd, 1H), 7.58 (dd, 1H), 7.50 (s, 1H), 7.23 (s, 1H), 7.15 (s, 1H), 3.84 (s, 2H).

Workup

  1. concentrationconcentrated
  2. additionWater (200 mL) and EtOAc (100 mL) were added
  3. customthe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3ae2ae1d90de413abf50c82b9e4110f9
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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