Perchloric Acid → 1,3-Dimethoxy-2-(Tol-2-yl)-4-Bromobenzene

HRID 324933Notes

Reaction equation

HRID 324933 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].[Br:18]N1C(=O)CCC1=O.Cl(O)(=O)(=O)=O>ClCCl>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][C:8]([Br:18])=[C:3]([O:2][CH3:1])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 67184N-bromobutanimideHCID 154981521,3-Dimethoxy-2-(Tol-2-yl)-Benzene

Product 1

HCID 155090951,3-Dimethoxy-2-(Tol-2-yl)-4-BromobenzeneYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Dimethoxy-2-(tol-2-yl)-benzene 1, (10 g, 43.86 mmol), N-bromosuccinimide (8.26 g, 46.4 mmol), and perchloric acid (70%, 0.5 ml) were mixed in dichloromethane (200 ml) and stirred for 4 hrs at room temperature. The reaction mixture was quenched with sodium bicarbonate solution (5%, 100 ml), the dichloromethane layer was washed with water (100 ml), brine (100 ml), and the solvent was removed. The crude product was purified by silica-gel chromatography eluting with hexane and ethyl acetate (0% to 10% ethyl acetate) yielding 10.8 g (80%) of 2.

Workup

  1. customThe reaction mixture was quenched with sodium bicarbonate solution (5%, 100 ml)
  2. washthe dichloromethane layer was washed with water (100 ml), brine (100 ml)
  3. customthe solvent was removed
  4. customThe crude product was purified by silica-gel chromatography
  5. washeluting with hexane and ethyl acetate (0% to 10% ethyl acetate)

Sources & evidence

ORD record
ord-54d2f12425db4b609336c9ccb1ae8294
Source dataset
uspto-grants-2001_04
Patent number
US06221604B1

Reaction notes

Loading…