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

HRID 599788Notes

Reaction equation

HRID 599788 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

A solution of 12.7 mL (247 mmol) bromine in 10 mL chloroform was added dropwise at RT 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 on Na2SO4 and concentrated by evaporation 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. customdried on Na2SO4
  5. concentrationconcentrated by evaporation i.vac
  6. customColumn chromatography (silica gel, Cyc/EtOAc 9:1) yielded the product

Sources & evidence

ORD record
ord-a48b1d0f07e84755b68e1a5eb497d2af
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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