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

HRID 1765854

Reaction equation

HRID 1765854 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bfb2078533f5429585da6db4c1f6edd2
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Linked notes

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