Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyridine

HRID 3309

反応式

HRID 3309 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16](Br)[CH:17]=1.[NH4+].[Cl-]>CN(C=O)C.O>[CH2:3]([O:10][C:16]1[CH:15]=[N:14][CH:13]=[C:12]([Br:11])[CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 693693,5-Dibromopyridine

生成物 1

HCID 153891983-(Benzyloxy)-5-bromopyridine収率 72.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in mineral oil, 40.9 g, 1.0 mol) in DMF (800 mL) was cooled to 0° C., and benzyl alcohol (105 mL, 1.0 mol) was slowly added. After stirring for 1 hour at ambient temperature, 3,5-dibromopyridine (200.4 g, 846 mmol) was added and the mixture allowed to stir for 16 hours. Saturated NH4Cl solution (500 mL) was added followed by water (400 mL), and the mixture was extracted with Et2O (5×300 mL). The combined Et2O extracts were washed with 50% brine (6×300 mL), dried (MgSO4), concentrated and the residue recrystallized from Et2O to afford a white solid (161 g, 72%): 1H NMR (CDCl3, 300 MHz) δ5.10 (s, 2H), 7.50-7.35 (m, 6H), 8.37-8.27 (m, 2H); MS (CI/NH3) m/z: 264/266 (M+H)+.

後処理

  1. stirringto stir for 16 hours
  2. extractionthe mixture was extracted with Et2O (5×300 mL)
  3. washThe combined Et2O extracts were washed with 50% brine (6×300 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue recrystallized from Et2O

出典と根拠

ORDレコード
ord-4279b67233d44b409a5090ce4f747f2e
出典データセット
uspto-grants-1998_03
特許番号
US05733912

関連ノート

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