Water → 2-Bromo-5-methoxy-1,3-dimethylbenzene

HRID 537469Notes

Reaction equation

HRID 537469 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].IC.[C:13](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:13])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 2359922-Bromo-5-methoxy-1,3-dimethylbenzeneYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 4-bromo-3,5-dimethylphenol (1.00 g, 4.98 mmol) in DMF (10.0 mL) was added iodomethane (1.41 g, 9.96 mmol) and potassium carbonate (1.37 g, 9.96 mmol). The mixture was stirred for 5 h at room temperature. The mixture was poured into water and extracted with ethyl acetate (15 ml*3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give 2-bromo-5-methoxy-1,3-dimethylbenzene (1.00 g) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 6.57 (s, 2H), 3.69 (s, 3H), 2.31 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate (15 ml*3)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8e67ef1441cc4d4da6f3c1593db76861
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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