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

HRID 1874933노트

반응식

HRID 1874933 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3ae2ae1d90de413abf50c82b9e4110f9
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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