2-tert-Butyl-4-methylphenol → 2-Bromo-4-methyl-6-tert-butylphenol
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
Product 1
Reagents, catalysts & solvents 1
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
- washthe crude mixture is washed with H2O
- dry with materialdried over MgSO4
- filtrationfiltered
- 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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