Sulfuric Acid → 4-Bromo-2-(tert-butyl)-5-methylphenol

HRID 1765854

反応式

HRID 1765854 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[CH3:10][C:11](O)([CH3:13])[CH3:12].S(=O)(=O)(O)O>ClCCl>[Br:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[C:6]([C:11]([CH3:13])([CH3:12])[CH3:10])[CH:7]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 728574-Bromo-m-cresol

生成物 1

HCID 187986984-Bromo-2-(tert-butyl)-5-methylphenol収率 51%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-bromo-3-methylphenol (Aldrich, 5.1 g, 27.3 mmol) in anhydrous dichloromethane (50 mL) was treated with 2-methyl-2-propanol (15 mL) and concentrated sulfuric acid (3 mL) and stirred at ambient temperature for 3 months. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography using 3–5% ethyl acetate in hexane as the eluent afforded the title compound as a deep yellow oil (3.42 g, 51%). It was used as such for the next step.

後処理

  1. customThe volatiles were evaporated in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil

出典と根拠

ORDレコード
ord-bfb2078533f5429585da6db4c1f6edd2
出典データセット
uspto-grants-2007_06
特許番号
US07226951B2

関連ノート

読み込み中…