Water → 1-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

HRID 1359193ノート

反応式

HRID 1359193 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=[CH:5]2.C([O-])(=O)C.[K+].[Br:32]Br.O>C(O)(=O)C>[Br:32][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:12]1[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:8]2

参加物

6

反応物 4

HCID 962WaterHCID 24408BromineHCID 517044Potassium AcetateHCID 113368791-[2-(6-Hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

生成物 1

HCID 113846851-[2-(5-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone収率 94.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

To an ice-cooled mixture of 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (1.59 g, 4.62 mmol) in glacial acetic acid (50 mL) was added potassium acetate (4.54 g, 46.2 mmol). The mixture was stirred at room temperature for 15 minutes and then chilled again in an ice bath. Bromine (0.27 mL, 5.3 mmol) in acetic acid (6 mL) was added dropwise. The mixture was stirred at room temperature for 15 minutes. It was poured into excess water and filtered. The precipitate was dissolved in ethyl acetate, with some warming, and dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to dryness to afford 1-[2-(5-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone as a yellow solid (1.85 g), mp 171-172° C. Mass spectrum (+APCl, [M+H]+) m/z 423. 1HNMR (400 MHz, DMSO-d6): δ10.95 (s, 1H), 8.4 (d, 1H, J=1.7 Hz), 8.15 (d, 1H, J=9.0 Hz), 8.05-8.1 (m, 2H), 7.95 (dd, 1H, J=8.8 Hz and 2.0 Hz), 7.7-7.75 (m, 1H), 7.35-7.45 (m, 3H), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C23H19BrO3. 0.25 H2O: Calculated: C, 64.57; H, 4.59; N, 0.00. Found: C, 64.19; H, 4.26; N, 0.05.

後処理

  1. temperaturechilled again in an ice bath
  2. stirringThe mixture was stirred at room temperature for 15 minutes
  3. filtrationfiltered
  4. dissolutionThe precipitate was dissolved in ethyl acetate, with some warming
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-649c7ac4388c42689c771ec990d65a35
出典データセット
uspto-grants-2003_07
特許番号
US06599925B2

反応ノート

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