Benzyl Bromide → 2-Benzyloxy-3-bromopyridine

HRID 1394865ノート

反応式

HRID 1394865 の反応式
[Br:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH2:11]([O:8][C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][N:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178517701HCID 178517701、化合物

生成物 1

HCID 147124562-Benzyloxy-3-bromopyridine収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-bromo-2-hydroxypyridine (1.74 g, 10 mmol) was added to a suspension of NaH (440 mg of 60% dispersion in mineral oil, 11 mmol) in DMF (10 mL), and the resultant mixture was stirred at rt for 30 min. Benzyl bromide (1.3 mL, 11 mmol) was then added, and the reaction was stirred at rt overnight. It was then quenched by the addition of water, and the product extracted with ethyl acetate (2×50 mL). The extracts were combined, washed with 1N HCl solution, then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography using hexanes to 100% ethyl acetate in hexanes as eluent to give the title compound as a colorless thick oil, (1.37 g, 52% yield). MS m/z 264, 266(MH+); 1H NMR (500 MHz, CDCl3) δ ppm 5.17 (s, 2 H) 6.05 (t, J=7.02 Hz, 1 H) 7.27-7.88 (m, 6 H) 7.70 (dd, J=7.17, 1.98 Hz, 1 H)

後処理

  1. customIt was then quenched by the addition of water
  2. extractionthe product extracted with ethyl acetate (2×50 mL)
  3. washwashed with 1N HCl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-96ced22ab29b4a39bb6ae9e38c2660fb
出典データセット
uspto-grants-2008_03
特許番号
US07348425B2

反応ノート

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