3,4-Dimethylphenol → 2-Bromo-4,5-dimethylphenol

HRID 1400738Notes

Reaction equation

HRID 1400738 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:10]Br.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:10][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=1[OH:9]

Participants

5

Reactant 3

HCID 72493,4-DimethylphenolHCID 24408BromineHCID 24437Sodium Sulfite

Product 1

HCID 1409612-Bromo-4,5-dimethylphenolYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,4-dimethylphenol (2 g, 16.37 mmol) in DCM (10 mL) at −78° C. was added bromine (0.843 mL, 16.37 mmol) dropwise and the reaction was stirred for 1 h at this temperature. Sat. sodium sulfite solution was added and it was then stirred 5 min at rt and then extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain 2 g oil. It was then purified with 5% EtOAc/hexane to isolate 800 mg (24%) of the desired product as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.22 (s, 1H), 6.84 (s, 1H), 5.33-5.23 (m, 1H), 2.20 (s, 3H), 2.19 (s, 3H).

Workup

  1. stirringit was then stirred 5 min at rt
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-50a4ae7ebbec43b581be139dce44b8b3
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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