4-Isopropylresorcinol → 4-Bromo-6-(propan-2-YL)benzene-1,3-diol

HRID 1947172Notes

Reaction equation

HRID 1947172 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11])([CH3:3])[CH3:2].[Br-:12].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl>[Br:12][C:8]1[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([OH:11])=[CH:6][C:7]=1[OH:10]

Participants

4

Reactant 2

HCID 901354-IsopropylresorcinolHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 598299224-Bromo-6-(propan-2-YL)benzene-1,3-diolYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-isopropyl-benzene-1,3-diol (IMO-a: 9.13 g, 60 mmol) and benzyltrimethyl ammoniumtribromide (24.6 g, 63 mmol) and methylene chloride 250 mL were placed in a 500 mL three-neck flask and were stirred at room temperature for 4 hours. After the reaction was finished, the reaction mixture was washed twice with saturated ammonium chloride and once with saturated sodium chloride, and then dried over anhydrous sodium sulfate. After filtration and evaporation, the residue was purified by silica gel column chromatography to obtain the title compound (IM1-a: 10.5 g, 76%).

Workup

  1. washthe reaction mixture was washed twice with saturated ammonium chloride and once with saturated sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration and evaporation
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-50990841d12049e8b3139ef576e9433b
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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