Bromine → 6-Bromo-7-(1,1-dimethylethyl)-2-(trifluoromethyl)-2h-1-benzopyran-3-carboxylic acid

HRID 650152노트

반응식

HRID 650152 반응식
[CH3:1][C:2]([C:5]1[CH:21]=[CH:20][C:8]2[CH:9]=[C:10]([C:17]([OH:19])=[O:18])[CH:11]([C:13]([F:16])([F:15])[F:14])[O:12][C:7]=2[CH:6]=1)([CH3:4])[CH3:3].[Br:22]Br>[Fe].C(Cl)(Cl)Cl>[Br:22][C:21]1[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:6][C:7]2[O:12][CH:11]([C:13]([F:14])([F:15])[F:16])[C:10]([C:17]([OH:19])=[O:18])=[CH:9][C:8]=2[CH:20]=1

참가 물질

5

반응물 2

HCID 24408BromineHCID 99044067-(1,1-Dimethylethyl)-2-trifluoromethyl-2h-1-benzopyran-3-carboxylic acid

생성물 1

HCID 218836796-Bromo-7-(1,1-dimethylethyl)-2-(trifluoromethyl)-2h-1-benzopyran-3-carboxylic acid

시약·촉매·용매 2

HCID 23925Iron촉매HCID 6212Chloroform용매

실험 절차

7-(1,1-Dimethylethyl-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylic acid (Example 12)(0.6 g, 2 mmol), chloroform (50 mL), iron filings (0.01 g, 0.2 mmol), and bromine (0.48 g, 3.00 mmol) were stirred at reflux for 16 h. The mixture was allowed to cool and was washed with brine (2×50 mL). After drying over MgSO4, the mixture was filtered, concentrated in vacuo, and the residue crystallized from ether-hexanes yielding the title compound as a white solid (0.5 g, 66%): ° p 198.6-199.9° C. 1H NMR (acetone-d6/3(d MHz) 7.85 (s, 1H), 7.72 (s, 1H), 7.13 (H, 1H) 5.83 (q, 1H, J=7.2 Hz), 1.5(s, 9H). Anal. Calc'd for C15H14O3F3Br: C, 47.52; H, 3.72; N, 21.07. Found: C, 47.42; H. 3.68; N. 21.15.

후처리

  1. temperatureat reflux for 16 h
  2. temperatureto cool
  3. washwas washed with brine (2×50 mL)
  4. dry with materialAfter drying over MgSO4
  5. filtrationthe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. customthe residue crystallized from ether-hexanes yielding the title compound as a white solid (0.5 g, 66%)
  8. custom198.6-199.9° C

출처 및 근거

ORD 기록
ord-6228372c09f44476b26ae650da9ed204
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271253B1

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