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Water → 1-Bromo-6-(4-hydroxy-phenyl)-naphthalen-2-ol

HRID 1830628
ノート
印刷プレビュー

反応式

HRID 1830628 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([OH:18])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1.O>C(#N)C>[Br:26][C:14]1[C:15]2[C:10](=[CH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)=[CH:17][CH:16]=2)[CH:11]=[CH:12][C:13]=1[OH:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 114590066-(4-Hydroxyphenyl)-2-naphthol

生成物 1

HCID 101496841-Bromo-6-(4-hydroxy-phenyl)-naphthalen-2-ol収率 100%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a solution of 6-(4-hydroxyphenyl)-2-naphthol (4.02 g, 17.0 mmol) in acetonitrile (150 mL) at 0° C. was added NBS (3.03 g, 17.0 mmol). The reaction was stirred at 0° C. for 3 hr and then poured into water (200 mL) and extracted with ethyl acetate (3×300 mL), The combined organic layers were washed with water, dried over sodium sulfate, filtered, evaporation of the solvent, and purification by silica column chromatography (20% ethyl acetate hexanes) yielded 5.33 g (100%) of the title compound as a tan solid. The title compound was further purified by reverse phase HPLC to yield a white solid: mp 208–210° C.; 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.47 Hz), 7.28 (1H; d, J=8.80 Hz), 7.63 (2H, d, J=8.50 Hz), 7.85 (2H, d, J=8.84 Hz), 8.02–8.06 (2H, m), 9.60 (1H, s), 10.54 (1H, s); MS (ESI) m/z 313/315 (M−H)−.

後処理

  1. extractionextracted with ethyl acetate (3×300 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporation of the solvent, and purification by silica column chromatography (20% ethyl acetate hexanes)

出典と根拠

ORDレコード
ord-0a8ebab8e53844379121951ef1f3825c
出典データセット
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07067524B2

反応ノート

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