Iodine → HCID 19783693, compound

HRID 1720109Notes

Reaction equation

HRID 1720109 reaction equation
[Mg:1].II.[CH3:4][O:5][C:6]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]([O:14][CH3:15])=[C:8]([CH3:16])[C:7]=1[Br:17]>CI.O1CCCC1>[Br-:17].[Mg+2:1].[CH3:4][O:5][C:6]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]([O:14][CH3:15])=[C:8]([CH3:16])[CH:7]=1.[Br-:17]

Participants

6

Reactant 3

HCID 807IodineHCID 2973651-Bromo-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 5462224Magnesium

Product 1

HCID 19783693HCID 19783693, compound

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

In an atmosphere of an argon stream, 1.1 g (0.045 mol) of magnesium, one drop of methyl iodide, and a catalytic amount of iodine were added to 30 ml of tetrahydrofuran, and further, a solution of 10.4 g (0.04 mol) of 2,5-dimethoxy-3,4,6-trimethyl-bromobenzene in 15 ml of tetrahydrofuran was added dropwise over 40 minutes while refluxing the tetrahydrofuran. The reaction was completed by refluxing for further 30 minutes, to thereby form 2,5-dimethoxy-3,4,6-trimethylbenzene magnesium bromide. Then, after cooling to 0° C., 580 mg (4.4 mmol) of the lactol compound (102) prepared in Example 1 was added and stirred at a room temperature for 2 hours, an aqueous sodium bicarbonate saturated solution was added to the reaction mixture, and an extraction with diethyl ether was carried out. The organic phase was washed with an aqueous sodium chloride saturated solution, and dried over anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure, and the residue was treated by silica gel column chromatography. Then, 1.35 g (98.5%) of the above-mentioned compound (103) was obtained from the ethyl acetate effluent as a colorless oil.

Workup

  1. temperatureby refluxing for further 30 minutes

Sources & evidence

ORD record
ord-2131b66ce80b48e2896ef24711f22530
Source dataset
uspto-grants-1996_04
Patent number
US05504219

Reaction notes

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