Sodium Carbonate → 2-Bromo-6-phenylpyridine

HRID 613221

반응식

HRID 613221 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 5686792-Bromo-6-phenylpyridine수율 76%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-35f85b64668d492f987465c0c41694d3
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008161

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