Diethanolamine → 3-(Ethylsulfanyl)phenol

HRID 724283ノート

反応式

HRID 724283 の反応式
B(Br)(Br)Br.[CH2:5]([S:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[CH:9]=1)[CH3:6].N(CCO)CCO>ClCCl>[CH2:5]([S:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[CH3:6]

参加物

5

反応物 3

HCID 8113DiethanolamineHCID 25134Boron tribromideHCID 6414391-(Ethylthio)-3-methoxybenzene

生成物 1

HCID 129052213-(Ethylsulfanyl)phenol収率 83.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Boron tribromide (1M in dichloromethane, 70 ml, 70 mmol) was added dropwise to a solution of 1-(ethylsulfanyl)-3-methoxybenzene (5.9 g, 35 mmol) in dichloromethane (150 ml) at 0° C. The mixture was allowed to warm to room temperature, stirred for 18 h then cooled to 0° C. A solution of diethanolamine (20 ml) in dichloromethane (40 ml) was added dropwise (Caution—strong exotherm!) and the mixture was stirred at ambient temperature for 15 min once addition was complete, then poured onto ice water. The mixture was extracted with dichloromethane and the organic phase was washed with 2N hydrochloric acid, water, dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by flash column chromatography using ethyl acetate:cyclohexane (20:80 to 30:70) as eluant to give 3-(ethylsulfanyl)phenol (4.53 g) as a colourless oil.

後処理

  1. temperaturethen cooled to 0° C
  2. stirringthe mixture was stirred at ambient temperature for 15 min
  3. additiononce addition
  4. additionpoured onto ice water
  5. extractionThe mixture was extracted with dichloromethane
  6. washthe organic phase was washed with 2N hydrochloric acid, water
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under reduced pressure
  9. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-7151596cf4334d4bba06624780a9d109
出典データセット
uspto-grants-2006_11
特許番号
US07141586B2

反応ノート

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