Methanol → 2-Bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene

HRID 505660Notes

Reaction equation

[Br:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][OH:17].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO>CN(C)C=O.O>[Br:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][O:17][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The above-obtained [2-bromo-3,5-bis(methoxymethoxy)phenyl]methanol (3.5 g, 11 mmol) was dissolved in N,N-dimethylformamide (20 mL) and cooled to 0° C. The obtained solution was added with 60% sodium hydride-oil dispersion (0.59 g, 15 mmol) and benzyl bromide (2.0 mL, 17 mmol), followed by stirring at a room temperature for 1 hour. The reaction mixture was added with methanol and water and extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1 to 10/1) to obtain 2-bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene (3.2 g, 70%).

Workup

extractionextracted with chloroform 3 times
washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1 to 10/1)

Sources & evidence

ORD record: ord-5334302b696f4a42ad884166bf4779dd
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781485B2

Reaction notes

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