3-Methoxy-4-methylaniline → HCID 21966452, compound

HRID 1790205Notes

Reaction equation

HRID 1790205 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[CH3:10])[NH2:6].[Br-:11].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>ClCCl>[Br:11][C:7]1[CH:8]=[C:9]([CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[NH2:6]

Participants

5

Reactant 3

HCID 278823-Methoxy-4-methylanilineHCID 516892Sodium BicarbonateHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 21966452HCID 21966452, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-4-methyl-aniline (8.19 g, 59.71 mmol) in dichloromethane (200 mL), was added tetrabutylammonium tribromide (28.79 g, 59.71 mmol) and the reaction mixture was stirred at room temperature for 2.5 hrs. Aqueous NaHCO3 was added and the layers separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 11.05 g of 2-bromo-5-methoxy-4-methyl-aniline (85% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.75 (s, 3 H), 3.95 (br s, 1 H), 6.27 (s, 1 H), 7.13 (s, 1 H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was further extracted with dichloromethane
  3. washthe combined organics washed successively with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6ae525a6995242d69c3583ae30f02c03
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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