Methyl iodide → 7-Bromo-1-methoxynaphthalene

HRID 402112Notes

Reaction equation

HRID 402112 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2O)=[CH:12][CH:11]=1>CC(C)=O>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[O:4][CH3:1])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 132157117-Bromonaphthalen-1-ol

Product 1

HCID 218659837-Bromo-1-methoxynaphthaleneYield 88.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

Potassium carbonate (3.3 g, 23.9 mmol) and methyl iodide (1.5 ml, 23.9 mmol) were added to a solution of the product from Step D (2.7 g, 11.9 mmol) in acetone (40 ml) at room temperature and the mixture was stirred at 65° C. for 2 hours. The solids were filtered, rinsed with ethyl acetate and the filtrate was evaporated. The residue was dissolved in ethyl acetate and washed with water twice. The aqueous layers were extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulfate to give 7-bromo-1-methoxynaphthalene (2.5 g, 88%) after chromatography (19:1 heptane/ethyl acetate): 1H NMR (300 MHz, CDCl3) δ 8.49 (d, J=2.1 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.59 (dd, J=8.7, 2.1 Hz, 1H), 7.39-7.43 (m, 2H), 6.85 (dd, J=5.4, 3.0 Hz, 1H), 3.15 (s, 3H).

Workup

  1. filtrationThe solids were filtered
  2. washrinsed with ethyl acetate
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water twice
  6. extractionThe aqueous layers were extracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-e9957a812650489c8efdb2b7e87cd4e6
Source dataset
uspto-grants-2014_06
Patent number
US08741901B2

Reaction notes

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