3,5-Dimethylphenol → 2-BroMo-3,5-diMethylphenol

HRID 1850392Notes

Reaction equation

HRID 1850392 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[C:14]([CH3:16])[CH:15]=1>C1(C)C=CC=CC=1>[Br:1][C:11]1[C:10]([CH3:9])=[CH:15][C:14]([CH3:16])=[CH:13][C:12]=1[OH:17]

Participants

4

Reactant 2

HCID 79483,5-DimethylphenolHCID 67184N-bromobutanimide

Product 1

HCID 183799822-BroMo-3,5-diMethylphenolYield 30,637.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-bromosuccinimide (178 g, 1.00 mmol) was slowly added to a solution of toluene (1.0 L) containing 3,5-dimethylphenol (122 g, 1.00 mol) under ice-cooling condition, and then the mixture was warmed to room temperature and stirred for 2 hours. The mixture was concentrated under reduced pressure, and then the residue was suspended in hexane (400 mL) to remove insolubles by filtration. The filtrate was concentrated, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1) to give 61.6 g of the title compound (yield: 31%).

Workup

  1. temperaturecooling condition
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto remove insolubles
  4. filtrationby filtration
  5. concentrationThe filtrate was concentrated
  6. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1)

Sources & evidence

ORD record
ord-416aa51f55524d0493b85ce4be390b84
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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