Methyl iodide → 4-Bromo-N,2-dimethylaniline

HRID 1791001Notes

Reaction equation

HRID 1791001 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:10][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 114234-Bromo-2-methylanilineHCID 11430Potassium Carbonate

Product 1

HCID 220425994-Bromo-N,2-dimethylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.03 g (10.91 mmol) of 4-bromo-2-methylaniline in 40 ml of DMF was added 2.07 g (14.98 mmol) of K2CO3 and 0.63 ml (10.12 mmol) of iodomethane, and the mixture was stirred at room temperature for 14 hours. After this time, the reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 20:1) to give the title compound. 1H-NMR (CDCl3) δ 2.18 (s, 3H), 2.90 (s, 3H), 3.60 (brs, 1H), 6.49 (d, J=8.6 Hz, 1H), 7.19 (s, 1H), 7.29 (d, J=8.5 Hz, 1H).

Workup

  1. customAfter this time, the reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 20:1)

Sources & evidence

ORD record
ord-af70023515324f95bea882d743822d1c
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

Loading…