tert-Butyl methyl ether → 1,3-Benzodioxole, 5-methoxy-

HRID 1602905Notes

Reaction equation

HRID 1602905 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1C.BrN1[C:17](=[O:18])CCC1=O.COC(C)(C)C.[C:26]([O-:29])(O)=[O:27].[Na+]>C(Cl)(Cl)(Cl)Cl>[CH3:17][O:18][C:8]1[CH:7]=[CH:6][C:5]2[O:27][CH2:26][O:29][C:4]=2[CH:9]=1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 33094Methyl o-toluateHCID 67184N-bromobutanimideHCID 516892Sodium Bicarbonate

Product 1

HCID 5924531,3-Benzodioxole, 5-methoxy-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl-2-methylbenzoate (3.00 g, 20.0 mmol) in carbon tetrachloride (15 ml) was added N-bromosuccinimide (3.55 g. 20.00 mmol). The reaction was allowed to stir at reflux for 3 h. The mixture was cooled and then partioned between t-butyl methyl ether and 5% NaHCO3. The combined organic extracts (×3) were washed with water, brine, and dried (MgSO4). Removal of the solvent under reduced pressure afforded the title compound as a white solid (4.60 g, quantitative yield). 1H NMR (400 MHz. CDCl13) δ 7.98 (d, 1H), 7.54-7.35 (mm, 3H), 4.98 (s, 2H), 3.98 (s. 3H)

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe mixture was cooled
  3. washThe combined organic extracts (×3) were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-28c5411aabe742e3aae691c08221704d
Source dataset
uspto-grants-1999_11
Patent number
US05985886

Reaction notes

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