Diethyl Ether → 3-(2,6-Dichloro-phenyl)-3H-[1,2,3]triazole-4-carbaldehyde

To a solution of [3-(2,6-dichloro-phenyl)-3H-[1,2,3]triazol-4-yl]-methanol (1.87 g, 1 equiv) in methylene chloride (110 mL) is added Dess-Martin oxidant (4.20 g, 1.3 equiv). The reaction mixture is allowed to stir at room temperature for 3 h. The reaction is incomplete as evidenced by TLC. The reaction mixture is treated with Dess-Martin oxidant (1.20 g). The reaction mixture is allowed to stir at room temperature for an additional 2 h. The reaction mixture is treated with 80 mL 1.5 N sodium hydroxide and 40 mL diethyl ether. The resulting solution is allowed to stir at room temperature for ten minutes. The reaction mixture is diluted with 120 mL water and extracted three times with chloroform. The combined organic layers are dried over magnesium sulfate and filtered though a plug of silica gel eluting with chloroform/ethyl acetate (3:1, 200 mL). The filtrate is concentrated under reduced pressure to give the title compound (1.76 g, 94%) as a white solid.

1. stirringto stir at room temperature for an additional 2 h
2. stirringto stir at room temperature for ten minutes
3. extractionextracted three times with chloroform
4. dry with materialThe combined organic layers are dried over magnesium sulfate
5. filtrationfiltered though a plug of silica gel eluting with chloroform/ethyl acetate (3:1, 200 mL)
6. concentrationThe filtrate is concentrated under reduced pressure

ORD record

ord-f4fdec5c5f3b49c58e0085fc5293ced5

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106077B2