1-Naphthol → 4-Bromonaphthalen-1-ol

HRID 1644214ノート

反応式

HRID 1644214 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:11])[CH:6]=1.[Br:12]N1C(=O)CCC1=O>CC#N>[Br:12][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10]([OH:11])=[CH:9][CH:8]=1

参加物

4

反応物 2

HCID 70051-NaphtholHCID 67184N-bromobutanimide

生成物 1

HCID 5756094-Bromonaphthalen-1-ol収率 64%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of naphthol (12, 5.0 g, 35 mmol) in CH3CN (125 mL) at 0° C. was added N-bromosuccinimide (7.9 g, 45 mmole) in several portions. The reaction mixture was warmed to room temperature, stirred for 1 h, and concentrated. The residue was dissolved in EtOAc (500 mL) and the solution was washed with water (300 mL) and brine (300 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, 4:1 hexanes/EtOAc) to afford 4-bromonaphthol (13, 5.0 g, 64%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.22-8.16 (m, 2H), 7.62-7.26 (m, 3H), 6.71 (d, J=8.0 Hz, 1H), 5.46 (s, 1H).

後処理

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc (500 mL)
  3. washthe solution was washed with water (300 mL) and brine (300 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, 4:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-3e50b182f21b4a688e5b4c737faa7dc3
出典データセット
uspto-grants-2012_02
特許番号
US08124607B2

反応ノート

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