Thionyl Chloride → HCID 90418861, compound

Temperature

0 °C

Into a 50-mL round-bottom flask, was placed [2-methoxy-6-(trifluoromethyl)phenyl]methanol (1.0 g, 4.85 mmol, 1.00 equiv), chloroform (10.0 g). This was followed by the addition of thionyl chloride (1.73 g, 14.54 mmol, 3.00 equiv) dropwise with stirring at 0° C. The resulting solution was stirred for 1 h at 30° C. The reaction progress was monitored by GCMS. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×15 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1.2 g (crude) of 2-(chloromethyl)-1-methoxy-3-(trifluoromethyl)benzene as yellow oil. This residue could be used for the next step directly.

1. customInto a 50-mL round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 1 h at 30° C
3. customThe reaction was then quenched by the addition of 10 mL of water
4. extractionThe resulting solution was extracted with 3×15 mL of dichloromethane
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. customThis resulted in 1.2 g (crude) of 2-(chloromethyl)-1-methoxy-3-(trifluoromethyl)benzene as yellow oil

ORD record

ord-494796d7414c4010bb5d357caed66935

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1