Bromine → 4-Bromo-2-ethyl-6-methylphenol

HRID 491128Notes

Reaction equation

HRID 491128 reaction equation
[Br:1]Br.[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12])[CH3:4].OS([O-])=O.[Na+]>C(Cl)(Cl)Cl>[Br:1][C:9]1[CH:8]=[C:7]([CH3:11])[C:6]([OH:12])=[C:5]([CH2:3][CH3:4])[CH:10]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 5193332-Ethyl-6-methylphenolHCID 23665763Sodium Bisulfite

Product 1

HCID 220068384-Bromo-2-ethyl-6-methylphenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

At RT a solution of 12.7 mL (247 mmol) bromine in 10 mL chloroform was added dropwise to a solution of 33.6 g (247 mmol) 2-ethyl-6-methyl-phenol in 350 mL chloroform and the mixture was stirred for 2 h. The reaction mixture was combined with an aqueous NaHSO3 solution and stirred for 20 min. The phases were separated and the organic phase was washed with saturated NaCl solution, dried over Na2SO4 and evaporated down i.vac. Column chromatography (silica gel, Cyc/EtOAc 9:1) yielded the product.

Workup

  1. stirringstirred for 20 min
  2. customThe phases were separated
  3. washthe organic phase was washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated down i.vac
  6. customColumn chromatography (silica gel, Cyc/EtOAc 9:1) yielded the product

Sources & evidence

ORD record
ord-8c2ab615cb5a4018a1f6f6954d6db7ce
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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