Dimethyl Sulfide → HCID 46737595, compound

Temperature

0 °C

Into a 100-mL 3-necked round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed 2-methoxy-6-(trifluoromethyl)benzoic acid (2.2 g, 9.99 mmol, 1.00 equiv), chlorobenzene (20 mL). This was followed by the addition of BH3.SMe2(2M in tetrahydrofuran) (15.0 mL) dropwise with stirring at 0° C. The mixture was stirred 15 min at 0° C. Then the resulting solution was stirred for 2 h at 80° C. and continued stirring for 18 h at 130° C. in an oil bath. The reaction progress was monitored by TLC (PE:EtOAc=4:1). The reaction was then quenched by the addition of 20 mL of water, extracted with 3×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2). This resulted in 1.9 g (92%) of [2-methoxy-6-(trifluoromethyl)phenyl]methanol as a yellow solid.

1. customInto a 100-mL 3-necked round-bottom flask (1 atm) purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. additionThis was followed by the addition of BH3
4. stirringThen the resulting solution was stirred for 2 h at 80° C.
5. stirringcontinued stirring for 18 h at 130° C. in an oil bath
6. customThe reaction was then quenched by the addition of 20 mL of water
7. extractionextracted with 3×20 mL of ethyl acetate
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under vacuum
10. customThis resulted in 1.9 g (92%) of [2-methoxy-6-(trifluoromethyl)phenyl]methanol as a yellow solid

ORD record

ord-56816cd34d3647f8a7ff961336331d53

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1