Bromine → 1-Bromo-2,3,4,5-tetramethoxy-6-methylbenzene

HRID 2268437Notes

Reaction equation

HRID 2268437 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[C:6]=1[O:16][CH3:17]>C(O)(=O)C>[Br:1][C:10]1[C:9]([CH3:11])=[C:8]([O:12][CH3:13])[C:7]([O:14][CH3:15])=[C:6]([O:16][CH3:17])[C:5]=1[O:4][CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 98777642,3,4,5-Tetramethoxytoluene

Product 1

HCID 125607691-Bromo-2,3,4,5-tetramethoxy-6-methylbenzeneYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (46.7 g, 0.292 mols) was dropwise added to a solution of 1,2,3,4-tetramethoxy-5-methylbenzene (51.6 g, 0.243 mols) in acetic acid (100 ml) at room temperature, and the reaction mixture was stirred for 15 minutes and then concentrated in vacuo. The residue was diluted with ethyl acetate, and the organic layer was washed with water, a saturated aqueous sodium bicarbonate solution, water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The thus-obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain the entitled compound (59.1 g) as an oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium bicarbonate solution, water and a saturated aqueous sodium chloride solution, then dried
  5. concentrationconcentrated in vacuo
  6. customThe thus-obtained crude product
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-06dce7c814e64274b58dc462733d890d
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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