Water → 2-Bromo-3-nitroanisole

HRID 1632018Notes

Reaction equation

HRID 1632018 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC.O>CN(C=O)C>[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 81672542-Bromo-3-nitrophenol

Product 1

HCID 177502992-Bromo-3-nitroanisoleYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-3-nitro-phenol synthesized above (11.5 mmol, 1.0 eq.) in DMF at room temperature was added cesium carbonate (13.8 mmol, 1.2 eq.), followed by iodomethane (33.7 mmol, 2.9 eq.), and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into water, stirred for 2 hours, filtered, the cake washed with two portions of water, and the resultant solid dried to afford 2-bromo-3-nitro-anisole (I-9, X═Br, R1═CH3) as a pale orange solid. Yield: 97%; 1H NMR (400 MHz; CDCl3): 3.97 (s, 3H), 7.07 (dd, J=8.4, 1.2 Hz, 1H), 7.32 (dd, J=8.0, 1.6 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H) ppm.

Workup

  1. filtrationfiltered
  2. washthe cake washed with two portions of water
  3. customthe resultant solid dried

Sources & evidence

ORD record
ord-d7378645770d4d0da2c4114ededdc1c5
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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