Methyl iodide → HCID 67172881, compound

HRID 1256098Notes

Reaction equation

HRID 1256098 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13].[H-].[Na+].[CH3:16]I>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][O:13][CH3:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67173430HCID 67173430, compound

Product 1

HCID 67172881HCID 67172881, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(2-bromo-5-nitrophenyl)ethanol (12 g, 48.7 mmol) in THF (100 mL) was cooled to 0° C., then NaH (2.53 g, 60%) was added slowly, followed by stirring at 0° C. for half an hour. Then MeI (33 mL, 487 mmol) was dropwise added, followed by stirring at room temperature overnight. The solvent was evaporated, water was added. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 1-bromo-2-(2-methoxyethyl)-4-nitrobenzene (10 g, yield 80%). 1H NMR: 400 MHz CDCl3 δ 8.15 (s, 1H), 7.95-7.92 (m, 1H), 7.72-7.70 (m, 1H), 3.68-3.65 (m, 2H), 3.37 (s, 3H), 3.12-3.09 (m, 2H).

Workup

  1. stirringby stirring at room temperature overnight
  2. customThe solvent was evaporated
  3. additionwater was added
  4. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7bc9e5a5f6b349bc8200b582f0c54e79
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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