Trifluoroacetic acid → HCID 18468176, compound

HRID 457946Notes

Reaction equation

HRID 457946 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[F:28])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][NH:19][C:18]([C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]([OH:30])=[O:5])=[O:29])=[C:22]([F:28])[CH:23]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22093497(2-(4-Bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid tert-butyl ester

Product 1

HCID 18468176HCID 18468176, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (2-(4-bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid tert-butyl ester in dichloromethane (11 mL, 0.2 M) was treated with trifluoroacetic acid (3.0 mL, 4.44 g. 39.0 mmol) and stirred for 24 h. The reaction was diluted with H2O and extracted with ethyl acetate (3×). The combined organic extracts were washed with H2O (2×), saturated aq NaCl, dried over MgSO4, filtered and concentrated to a crude solid that was recrystallized from heptane and ethyl acetate to give (2-(4-bromo-2-fluoro-benzylcarbamoyl)-4-nitro-phenoxy]-acetic acid as a white crystalline solid (0.98 g, 92%); Rf 0.10 (10% ethyl acetate in dichloromethane); 1H NMR (DMSO-d6, 300 MHz) δ 9.14 (br t, J=6.0 Hz, 1 H), 8.58 (d, J=3.3 Hz, 1 H), 8.34 (dd, J1=9.0 Hz, J2=3.0 Hz, 1 H), 7.52 (br dd, J, =9.3 Hz, J2=3.0 Hz, 1 H), 7.43–7.32 (m, 3 H), 5.02 (s, 2 H), 4.52 (d, J=6.0 Hz, 2H). ESI-LC/MS m/z calcd for C16H12BrFN2O6: 426.0 found 427.0 (M+1)+. Anal. calcd for C16H12BrFN2O6: C, 44.99; H, 2.83; N, 6.56. Found C, 44.97; H, 2.83; N, 6.47.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with H2O (2×), saturated aq NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a crude solid that
  6. customwas recrystallized from heptane and ethyl acetate

Sources & evidence

ORD record
ord-234e057188b5421eabff4935d0b82d9d
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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