Hydrochloric Acid → 1-Bromo-4-((methoxymethoxy)methyl)-2-methylbenzene

9.10 g of (4-bromo-3-methylphenyl)methanol was dissolved in 91 mL of methylene chloride and cooled to 5° C., to which 19.7 mL of N-ethyldiisopropylamine and 6.9 mL of chloromethyl methyl ether were successively added dropwise at 5 to 10° C., and then this mixture was stirred for 2.5 hours at room temperature. Water was added to the reaction mixture and adjusted to pH 7 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 10.44 g of 1-bromo-4-[(methoxymethoxy)methyl]-2-methylbenzene as yellow oil.

1. additionwere successively added dropwise at 5 to 10° C.
2. customthe organic phase was separated
3. washAfter the resultant organic phase was washed with water
4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate
5. distillationthe solvent was distilled out under reduced pressure
6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

ORD record

ord-fa73fd8dc7e148358f2dac96d08e4a5a

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772285B2