Methyl iodide → 1-Bromo-3-(methoxymethyl)-5-nitrobenzene

HRID 1039893Notes

Reaction equation

HRID 1039893 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.I[CH3:14].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][O:12][CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14866972(3-Bromo-5-nitrophenyl)methanol

Product 1

HCID 672485781-Bromo-3-(methoxymethyl)-5-nitrobenzeneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3-bromo-5-nitrophenyl)methanol (500 mg, 2.155 mmol) in DMF (7.2 mL) was added iodomethane (0.40 mL, 6.46 mmol. The solution was cooled to 0° C. before NaH (60% dispersion in mineral oil, 172 mg, 4.31 mmol) was added. The reaction was stirred at 0° C. and allowed to come to room temperature. After 2 hours the reaction was quenched with water and ethyl acetate was then added. Extraction was done with ethyl acetate (3×). The combined organic layer was dried over magnesium sulfate and then filtered. Ethyl acetate was then removed in vacuo to afford 1-bromo-3-(methoxymethyl)-5-nitrobenzene (470 mg, 1.910 mmol, 89% yield) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.25 (s, 1H), 8.13 (s, 1H), 7.96 (s, 1H), 4.53 (s, 2H), 3.33 (s, 3H).

Workup

  1. additionwas added
  2. customto come to room temperature
  3. customAfter 2 hours the reaction was quenched with water and ethyl acetate
  4. additionwas then added
  5. extractionExtraction
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customEthyl acetate was then removed in vacuo

Sources & evidence

ORD record
ord-b57f2546269a4285954050482c2308cb
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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