Methane, dichloromethoxy- → HCID 10632006, compound

Temperature

5 °C

5.25 ml of dichloromethyl methyl ether were dissolved in 40 ml dichloromethane and cooled to +5° C. 6.75 ml tin(IV)chloride were added neat over 45 min to the solution. After the addition the mixture was stirred for 45 min at 5° C. 11.4 g 4-fluoro-1-methoxy-naphthalene in 30 ml dichloromethane was added over 1 h. Then the cooling bath was removed, and the mixture was stirred for 2 h at ambient temperature. It was then poured into ice/water. The dichloromethane layer was separated and the aqueous phase was extracted with dichloromethane. The combined dichloromethane layers were washed with water, dried over sodium sulphate, filtered through celite and concentrated in vacuo. The residue was treated with pentane to yield 9.3 g of 4-fluoro-1-methoxynaphthalene-2-carbaldehyde as a brown solid.

1. temperaturecooled to +5° C
2. additionAfter the addition the mixture
3. customThen the cooling bath was removed
4. stirringthe mixture was stirred for 2 h at ambient temperature
5. additionIt was then poured into ice/water
6. customThe dichloromethane layer was separated
7. extractionthe aqueous phase was extracted with dichloromethane
8. washThe combined dichloromethane layers were washed with water
9. dry with materialdried over sodium sulphate
10. filtrationfiltered through celite and
11. concentrationconcentrated in vacuo
12. additionThe residue was treated with pentane

ORD record

ord-084da7805d334035a9d12affb9fe5e46

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552033B2