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

HRID 1874933ノート

反応式

HRID 1874933 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3ae2ae1d90de413abf50c82b9e4110f9
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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