2-tert-Butyl-4-methylphenol → 2-Bromo-4-methyl-6-tert-butylphenol

HRID 2261527Notes

Reaction equation

HRID 2261527 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].[Br:13]Br>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([Br:13])[C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 170042-tert-Butyl-4-methylphenolHCID 24408Bromine

Product 1

HCID 109884772-Bromo-4-methyl-6-tert-butylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-t-Butyl-4-methylphenol (10 g, 60.8 mmol) is dissolved in CH2Cl2 (300 mL). Bromine (3.1 mL, 60.8 mmol) is added dropwise to the solution. After 20 minutes, the crude mixture is washed with H2O, dried over MgSO4, filtered and rotovapped to give yellow oil: 12.6 g, 85%. 1H NMR (CDCl3) δ: 1.402 (s, 9H, t-Bu), 2.267 (s, 3H, CH3), 5.640 (s, 1H, OH), 7.017 (s, 1H, Ar), 7.167 (s, 1H, Ar).

Workup

  1. washthe crude mixture is washed with H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customto give yellow oil

Sources & evidence

ORD record
ord-797882cd13494660a7d156002f0b2b14
Source dataset
uspto-grants-2010_12
Patent number
US07847099B2

Reaction notes

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