Water → 4-Bromo-2-nitroanisole

HRID 1966482Notes

Reaction equation

HRID 1966482 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[H-].[Na+].[CH3:14]I.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:14])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 243644-Bromo-2-nitrophenolHCID 24758Sodium hydride

Product 1

HCID 1185334-Bromo-2-nitroanisoleYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2-nitrophenol (5.0 g, 23 mmol) and sodium hydride (0.6 g, 25.3 mmol) were suspended in DMF (50 ml). Methyl iodide (3.9 mL, 28 mmol) was added dropwise at room temperature and stirred for 30 minutes. Water was added slowly to reaction mixture to get precipitate of 4-bromo-2-nitroanisole (0.67 g), 90% yield. The crude solid that was used without further purification. 1H NMR (500 MHz, CDCl3): δ 3.98 (s, 3H), 7.03 (d, J=8.9 Hz, 1H), 7.68 (dd, J=2.45 Hz, 1H), 8.01 (d, J=2.45 Hz, 1H). 13C NMR (500 MHz, CDCl3): δ 56.9, 112.0, 115.3, 128.5, 137.1, 140.2, 152.3.

Sources & evidence

ORD record
ord-b97c4f2cc1244955b54c749598b1a3e2
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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