Sodium Phosphate, Dibasic → 3-Bromo-6-methoxy-2-methylpyridine

HRID 1372355ノート

反応式

HRID 1372355 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1.P([O-])([O-])(O)=O.[Na+].[Na+].[Br:17]Br>O>[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH3:9])[C:6]([Br:17])=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 24203Sodium Phosphate, DibasicHCID 24408BromineHCID 53247732-Methoxy-6-methylpyridine

生成物 1

HCID 107981463-Bromo-6-methoxy-2-methylpyridine収率 55.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2-methoxy-6-methylpyridine (17.0 g, 138 mmol) and a solution of disodium hydrogen phosphate (0.15M in water, 250 mL) was stirred at room temperature. Bromine (7.1 mL, 138 mmol) was added dropwise over 15 min via an addition funnel. The reaction mixture was then stirred at room temperature for 4 h. The clear colorless solution was diluted with water (500 mL) and extracted with dichloromethane (200 mL) three times. The combined organic layers were dried over MgSO4, filtered and solvent was removed in vacuo from the filtrate to give a yellow liquid. Flash chromatography on silica gel (EtOAc:hexane::1:20) and removal of solvent from the desired combined fractions afforded a clear colorless liquid (15.4 g): 1H-NMR(CDCl3, 300 MHz): δ 7.60 (d, 1H, J=8), 6.46 (d, 1H, J=8), 3.89 (s, 3H), 2.54 (s, 3H).

後処理

  1. extractionextracted with dichloromethane (200 mL) three times
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customsolvent was removed in vacuo from the filtrate
  5. customto give a yellow liquid
  6. customFlash chromatography on silica gel (EtOAc:hexane::1:20) and removal of solvent from the

出典と根拠

ORDレコード
ord-5eeeada7568f473986addad1092a0133
出典データセット
uspto-grants-2007_01
特許番号
US07157578B2

反応ノート

読み込み中…