Chloromethyl Methyl Ether → 5-Bromo-3-methoxy-2-(methoxymethoxy)benzaldehyde

Ethyldiisopropylamine (3.01 ml, 17.1 mmol) and methoxymethylchloride (1.5 ml, 15.7 mmol) were added to a dichloromethane solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.3 g, 14.3 mmol) under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→11:9). The purified product was concentrated to dryness under reduced pressure to obtain 5-bromo-3-methoxy-2-methoxymethoxybenzaldehyde (4.2 g) as light yellow solid.

1. washThe reaction solution was washed with water
2. dry with materialdried over magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→11:9)
5. concentrationThe purified product was concentrated to dryness under reduced pressure

ORD record

ord-d9f9d641b30a4b4b934e7049a3b737e3

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598162B2