Water → HCID 13163448、化合物

HRID 1776799ノート

反応式

HRID 1776799 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C(O)C.C(O)(=O)C.C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8]2[NH:18][C:12]3[C:17]([CH:9]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=1

参加物

7

反応物 3

HCID 962Water2 回HCID 7516PhenylhydrazineHCID 959915'-Bromo-2'-hydroxyacetophenone

生成物 1

HCID 13163448HCID 13163448、化合物収率 22.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 702Ethanol溶媒HCID 7237O-Xylene溶媒

実験手順

1-(5-bromo-2-hydroxyphenyl)ethanone (7.1 g, 33 mmol) and phenylhydrazine (4.3 g, 40 mmol) were stirred in 45 mL of dry ethanol. Acetic acid (27 drops) was added and the mixture was refluxed for 5 hours. After cooling to room temperature, the precipitates were collected by filtration to provide the crude product as a light yellow solid, which was stirred in 100 mL of xylene and 50 g of polyphosphoric acid at 85° C. for 8 hours. Water was added to the warm crude, and then the mixture was stirred for 10 minutes before poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (petroleum ether:EtOAc=10:1) provided 4-bromo-2-(1H-indol-2-yl)phenol as a light yellow powder (2.1 g, 22.1%). 1H-NMR (CDCl3, 400 MHz) δ 10.08 (s, 1H), 9.56 (s, 1H), 7.88 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.14˜7.19 (m, 2H), 7.08 (t, J=7.2 Hz, 1H), 6.8˜56.88 (m, 2H). MS (M+H)+: 288/290.

後処理

  1. temperaturethe mixture was refluxed for 5 hours
  2. filtrationthe precipitates were collected by filtration
  3. customto provide the crude product as a light yellow solid, which
  4. temperaturewarm crude
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography on silica gel (petroleum ether:EtOAc=10:1)

出典と根拠

ORDレコード
ord-a4c5ef70b0a949b0a493e5b0e790d8a0
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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