Dimethylformamide → 4-Bromo-2-chloroanisole

HRID 1668718Notes

Reaction equation

HRID 1668718 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[CH3:10]N(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+].IC>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:10])=[C:4]([Cl:9])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 198594-Bromo-2-chlorophenol

Product 1

HCID 30165374-Bromo-2-chloroanisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-2-chlorophenol (7.0 g, 33.0 mmol, 1 eq), N,N-dimethylformamide (50 mL) and cesium carbonate (8.5 g, 42.0 mmol, 1.2 eq) was stirred at room temperature then iodomethane (2.5 mL, 1.2 eq) was added. The mixture was heated to 50° C. overnight, cooled to room temperature and treated with water (500 mL). The reaction was extracted with dichloromethane, dried (sodium sulfate) and concentrated in vacuo. The crude was purified by flash chromatography eluting with cyclohexane. 7.5 g of clean product in a quantitative yield.

Workup

  1. temperatureThe mixture was heated to 50° C. overnight
  2. temperaturecooled to room temperature
  3. extractionThe reaction was extracted with dichloromethane
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography
  7. washeluting with cyclohexane

Sources & evidence

ORD record
ord-b971e9cfc6d743a5b320915168c94244
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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