Methanol → 4-Methoxy-3,5-bis(trifluoromethyl)benzonitrile

Temperature

30 °C

Into a 50-mL round-bottom flask, was placed methanol (10 mL) and cooled to 0° C. Na (337 mg, 14.65 mmol, 2.00 equiv) was added. When the Na was reacted completely, 4-chloro-3,5-bis(trifluoromethyl)benzonitrile (2.0 g, 7.31 mmol, 1.00 equiv) was added 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 3×20 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue could been used for the next step directly. This resulted in 1.33 g of 4-methoxy-3,5-bis(trifluoromethyl)benzonitrile as yellow oil. Mass spectrum (GC, m/z): Calcd. for C10H5F6NO, 269.0 (M). found 269.0.

1. customInto a 50-mL round-bottom flask, was placed
2. customThe reaction was then quenched by the addition of 10 mL of water
3. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
4. washThe resulting mixture was washed with 2×20 mL of sodium chloride
5. dry with materialThe mixture was dried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. customThis resulted in 1.33 g of 4-methoxy-3,5-bis(trifluoromethyl)benzonitrile as yellow oil

ORD record

ord-bb407ff1f1384d6b81e5fa4576ab822d

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1