Water → 1-Bromo-4-methoxy-2,5-dimethylbenzene

HRID 412631Notes

Reaction equation

HRID 412631 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH3:18].O.CCCCCCC>CN(C=O)C>[Br:8][C:14]1[C:13]([CH3:16])=[CH:12][C:11]([O:17][CH3:18])=[C:10]([CH3:9])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 67184N-bromobutanimideHCID 743502,5-Dimethylanisole2×

Product 1

HCID 27525981-Bromo-4-methoxy-2,5-dimethylbenzeneYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of NBS (306.9 g, 1.724 mol, 1.1 equiv) in DMF (850 mL) was treated dropwise with 2,5-dimethylanisole (4, 213.2 g, 220.9 mL, 1.567 mol) at 25° C. under N2. The reaction temperature was maintained under 60° C. during the addition of 2,5-dimethylanisole. The resulting reaction mixture was stirred at room temperature for an additional 1 h before being treated with H2O (2000 mL) and heptane (1000 mL). The two layers were separated and the aqueous layer was extracted with heptane (500 mL). The combined organic extracts were washed with H2O (4×800 mL), and saturated NaCl solution (500 mL), dried over MgSO4, and concentrated in vacuo. The crude product (5, 329.8 g, 336.9 g theoretical, 97.9%) was obtained as pale-yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted with heptane (500 mL)
  4. washThe combined organic extracts were washed with H2O (4×800 mL), and saturated NaCl solution (500 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b44b3613ec564c0eb9a6dd1242c45a47
Source dataset
uspto-grants-2003_05
Patent number
US06562965B1

Reaction notes

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