Hydrogen Bromide → 2-Bromo-1-(5-ethylthiophen-3-yl)ethanone

HRID 453690ノート

反応式

HRID 453690 の反応式
[CH2:1]([C:3]1[S:7][CH:6]=[C:5]([C:8](Cl)=[O:9])[CH:4]=1)[CH3:2].[N+](=[CH:13][Si](C)(C)C)=[N-].[BrH:18].C(=O)(O)[O-].[Na+]>CC#N>[Br:18][CH2:13][C:8]([C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[S:7][CH:6]=1)=[O:9]

参加物

6

反応物 4

HCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 516892Sodium BicarbonateHCID 133561385-Ethylthiophene-3-carbonyl chloride

生成物 1

HCID 585569202-Bromo-1-(5-ethylthiophen-3-yl)ethanone収率 32.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

5-Ethylthiophene-3-carbonyl chloride (224 mg, 1.28 mmol) was dissolved in dry CH3CN (10 ml) and cooled at 0° C., under nitrogen atmosphere. (Diazomethyl)-trimethylsilane (1.92 ml, 3.85 mmol, 2M in hexane) was slowly added, and the resulting reaction was stirred at room temperature for 18 hours. Then the reaction was cooled at 0° C. and 48% HBr was added dropwise. The reaction was stirred at 0° C. for 2 hours. Smashed ice was added to the mixture, and then sodium bicarbonate was added until pH is about 7. The solution was extracted with EtOAc, and the organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The crude was purified by flash chromatography (Petroleum ether/EtOAc=9/1) to obtain 2-bromo-1-(5-ethylthiophen-3-yl)ethanone (97 mg, 32.4% yield).

後処理

  1. customthe resulting reaction
  2. temperatureThen the reaction was cooled at 0° C.
  3. stirringThe reaction was stirred at 0° C. for 2 hours
  4. additionSmashed ice was added to the mixture
  5. extractionThe solution was extracted with EtOAc
  6. customthe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude was purified by flash chromatography (Petroleum ether/EtOAc=9/1)

出典と根拠

ORDレコード
ord-b1e6217d49484f49b82a2c67aeb0d503
出典データセット
uspto-grants-2013_07
特許番号
US08492548B2

反応ノート

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