Methyl iodide → 2-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene

Under cooling in an ice water bath, to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (118.8 g) in N,N-dimethylformamide (960 mL) was added sodium hydride (60% oily; 24.7 g), and the mixture was stirred for 10 minutes. To this iodomethane (41.7 mL) was dropped. Thereafter, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water (2.5 L), and extracted with ethyl acetate. The resulting organic layer was washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography, and from a fraction of n-hexane:ethyl acetate (4:1), 121.3 g of a title compound was obtained as colorless oil.

1. stirringThereafter, the reaction mixture was stirred at room temperature for 1 hour
2. extractionextracted with ethyl acetate
3. washThe resulting organic layer was washed with saturated saline
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-3f0c0546acf446428f9a1afd11c5b86c

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858809B2