Phosphorus oxide (P4O10) → 4-FLUOROBENZOYL CYANIDE

4-Fluorobenzoyl cyanide was prepared according to the general procedure reported by G. A. Olah et al. [supra]. Under dry conditions, 1.829 g of 4-fluorobenzoyl chloride (98%, Aldrich) (11.54 mmol), 30 mL of methylene chloride, freshly distilled from phosphorus pentoxide under nitrogen, and 1.8 mL of trimethylsilyl cyanide (13 mmol) were added to a 100-mL round bottom flask. To this solution 0.29 mL of tin (IV) chloride (2.5 mmol) was added. On addition of the tin (IV) chloride, the color of the solution changed from clear to dark yellow and within 5 min the color of the solution was dark brown. The reaction mixture was stirred for 2 hr at room temperature, then quenched with 90 mL of ice-cold water, and finally extracted with two 90-mL portions of methylene chloride. The methylene chloride extracts were combined, washed with two 90-mL portions of ice-cold water, dried with MgSO4, and filtered. The methylene chloride was removed by rotary evaporation. The dark brown residue which resulted was stirred with pentane. The pentane solution was decanted and the pentane removed by rotary evaporation to yield 0.911 g of 4-fluorobenzoyl cyanide as a yellow oil. The product was further purified by Kugelrohr vacuum distillation which afforded 0.666 g (39%) of 4-fluorobenzoyl cyanide as a colorless oil that solidified on standing in the freezer: IR (CCl4) (partial) 2220, 1685, 1600, 1505, 1410 cm-1.

1. custom4-Fluorobenzoyl cyanide was prepared
2. customwithin 5 min
3. customquenched with 90 mL of ice-cold water
4. extractionfinally extracted with two 90-mL portions of methylene chloride
5. washwashed with two 90-mL portions of ice-cold water
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. customThe methylene chloride was removed by rotary evaporation
9. customThe dark brown residue which resulted
10. customThe pentane solution was decanted
11. customthe pentane removed by rotary evaporation

ORD record

ord-20245fe603954e1e81f33919b219de78

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04942247