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

HRID 722306ノート

反応式

HRID 722306 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 6212Chloroform溶媒

実験手順

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%): mp 198.6–199.9° C. 1H NMR (acetone-d6/300 MHz) 7.85 (s, 1H), 7.72 (s, 1H), 7.13 (s, 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.

後処理

  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%)

出典と根拠

ORDレコード
ord-49fdd2dd0f584050b6c56ba7c407150b
出典データセット
uspto-grants-2006_11
特許番号
US07138411B2

反応ノート

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