Water → 2-Fluoro-4-formylbenzonitrile

To a solution of α,α-dibromo-4-cyano-3-fluorotoluene, as described above in Step B, (5.60 g, 19.1 mmol) in EtOH (255 mL) and water (45 mL) was added AgNO3. The mixture was heated to reflux for 3 hrs, then stood at ambient temperature for 18 hrs, then the solid was removed by filtration and the filtrate was concentrated under reduced pressure to a volume of approximately 20 mL. Water (30 mL) was added, and the mixture was concentrated to dryness in vacuo. The residue was partitioned between sat. aq. NaHCO3 (20 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted further with CH2Cl2 (2×50 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dried for several days at ca. 0.5 mm Hg to yield the desired aldehyde as a pale solid.

1. temperatureThe mixture was heated
2. temperatureto reflux for 3 hrs
3. customthe solid was removed by filtration
4. concentrationthe filtrate was concentrated under reduced pressure to a volume of approximately 20 mL
5. additionWater (30 mL) was added
6. concentrationthe mixture was concentrated to dryness in vacuo
7. customThe residue was partitioned between sat. aq. NaHCO3 (20 mL) and CH2Cl2 (50 mL)
8. extractionThe aqueous layer was extracted further with CH2Cl2 (2×50 mL)
9. dry with materialThe combined organic extracts were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was dried for several days at ca. 0.5 mm Hg

ORD record

ord-5d52f39a7f834801b776e08a88d676e8

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06358985B1