Methyl iodide → 2-Bromo-3-nitroanisole

HRID 562863

Reaction equation

HRID 562863 reaction equation
[N+]([C:4]1C=CC=CC=1O)([O-])=O.[Br:11][C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][C:13]=1[OH:21].C(=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[Br:11][C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][C:13]=1[O:21][CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 69472-NitrophenolHCID 10796Cesium carbonateHCID 81672542-Bromo-3-nitrophenol

Product 1

HCID 177502992-Bromo-3-nitroanisoleYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The nitrophenol starting material B2 (3.1 g; 14.2 mmol) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1 mmol) followed by MeI (2.6 mL; 42.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1×200 mL), washed with water (1×200 mL), brine (4×100 mL), dried (MgSO4), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole B3 (94%; 3.1 g) as an orange solid.

Workup

  1. customThe DMF was evaporated
  2. washwashed with water (1×200 mL), brine (4×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-62fe4f27dc5a4e17be77b4c04519d7bf
Source dataset
uspto-grants-2011_11
Patent number
US08067438B2

Linked notes

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