Methyl iodide → 2-Bromo-5-methoxy-1,3-dimethylbenzene

HRID 1169521Notes

Reaction equation

HRID 1169521 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[C:11](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:11])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

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

Product 1

HCID 2359922-Bromo-5-methoxy-1,3-dimethylbenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 4-bromo-3,5-dimethyl-phenol (40.2 g, 0.200 mol) and potassium carbonate (55.2 g, 0.400 mol) in acetone (200 mL) was added methyl iodide ( 24.9 mL, 0.600 mol) at room temperature under N2. The reaction mixture was then refluxed at 65° C. for 8 h. After cooling to room temperature, the mixture was filtered, and the filtrate was concentrated in vacuo. The resulting clear liquid was distilled under reduced pressure (70° C./0.1 Torr) to give 42.4 g (99%) of title compound as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ 6.663 (s, 2H), 3.778 (s, 3H), 2.402 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 158.165, 139.203, 118.357, 113.953, 55.520, 24.319. MS (EI): m/z 214 [M+, 79Br 100], 216 [M+, 79Br, 96].

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. distillationThe resulting clear liquid was distilled under reduced pressure (70° C./0.1 Torr)

Sources & evidence

ORD record
ord-11770c2463404d1ab2e743a2e55145a1
Source dataset
uspto-grants-2010_11
Patent number
US07824582B2

Reaction notes

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