Methyl iodide → 2-Chloro-1-methoxy-3-nitrobenzene

HRID 562866Notes

Reaction equation

HRID 562866 reaction equation
[N+]([C:4]1C=CC=CC=1O)([O-])=O.[Cl: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>[Cl: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 3013917Phenol, 2-chloro-3-nitro-

Product 1

HCID 124118272-Chloro-1-methoxy-3-nitrobenzeneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The nitrophenol starting material C2 (1.3 g; 7.49 mmol) was dissolved in DMF (10 mL) and to this solution was added ground cesium carbonate (2.92 g; 8.96 mmol), followed by MeI (1.4 mL; 22.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated in vacuo and the residue taken up in ether (150 mL), washed with water (150 mL), brine (4×100 mL), and then dried over (MgSO4). The organic phase was filtered and evaporated to afford the crude 2-chloro-3-nitroanisole C3 (98%; 1.38 g) as an orange solid. Homogeneity by HPLC (TFA) @ 220 nm: 93%.

Workup

  1. customThe DMF was evaporated in vacuo
  2. washwashed with water (150 mL), brine (4×100 mL)
  3. dry with materialdried over (MgSO4)
  4. filtrationThe organic phase was filtered
  5. customevaporated

Sources & evidence

ORD record
ord-4c8d32eb7429488982b09ad613473bcd
Source dataset
uspto-grants-2011_11
Patent number
US08067438B2

Reaction notes

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