Sodium Carbonate → 2-Bromo-6-phenylpyridine

HRID 613221

反応式

HRID 613221 の反応式
[C:1]1([C:7]2[NH:12][C:11](=O)[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:16])=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:16][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 878896-Phenyl-2-pyridone

生成物 1

HCID 5686792-Bromo-6-phenylpyridine収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 6-phenyl pyridone (3 g, 17.5 mmol; prepared according to Example 6) and phosphoryl bromide (7.2 g, 25.0 mmol) is heated to 100° C. for 5 h. The cooled mixture is poured into water (40 ml) and the pH is adjusted to 9 by addition of saturated aqueous sodium carbonate. Then the layers are separated and the aqueous layer is extracted with ethyl acetate (50 ml). The combined organic layers are dried with anhydrous magnesium sulphate and the solvent is evaporated in vacuo. The crude product is crystallized from aqueous ethanol. Subsequent purification by flash chromatography (silica gel, hexane/ethyl acetate 9/1 v/v) gives 2-bromo-6-phenyl pyridine (3.1 g, 76% of th.) as light brown crystals with mp 50° C.

後処理

  1. customThen the layers are separated
  2. extractionthe aqueous layer is extracted with ethyl acetate (50 ml)
  3. dry with materialThe combined organic layers are dried with anhydrous magnesium sulphate
  4. customthe solvent is evaporated in vacuo
  5. customThe crude product is crystallized from aqueous ethanol
  6. customSubsequent purification by flash chromatography (silica gel, hexane/ethyl acetate 9/1 v/v)

出典と根拠

ORDレコード
ord-35f85b64668d492f987465c0c41694d3
出典データセット
uspto-grants-1999_12
特許番号
US06008161

関連ノート

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