Methane, dichloromethoxy- → 5-iodo-2-methoxybenzaldehyde

Temperature

0 °C

To a solution of 2.04 grams (8.72 mmol) of 4-iodoanisole in 36 mL of CH2Cl2, cooled to 0° C., was added dropwise 2.0 mL (18.7 mmol) of titanium tetrachloride. After stirring for 30 min., 0.93 mL (10.3 mmol) of α, α-dichloromethyl methyl ether was added and the reaction maintained at 0° C. for another 2 hours. The reaction mixture was then poured with stirring into a mixture of 50 mL of CH2Cl2 and 50 mL of saturated aqueous sodium bicarbonate (NaHCO3). After 30 min., this was filtered through diatomaceous earth, the organic layer was separated, the aqueous layer was twice extracted with CH2Cl2, and all of the organic layers were combined, dried with MgSO4 and concentrated in vacuo. The crude residue was recrystallized from ethanol (EtOH) to give 5-iodo-2-methoxybenzaldehyde as pale yellow needles, 1.37 grams (60%).

1. additionThe reaction mixture was then poured
2. waitAfter 30 min.
3. filtrationthis was filtered through diatomaceous earth
4. customthe organic layer was separated
5. extractionthe aqueous layer was twice extracted with CH2Cl2
6. dry with materialdried with MgSO4
7. concentrationconcentrated in vacuo
8. customThe crude residue was recrystallized from ethanol (EtOH)

ORD record

ord-0b39e2fa449640e5ae829c8d69502c5e

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369074B1