Cyanuric chloride → HCID 58065263, compound

Temperature

-78 °C

A solution of n-BuLi (15 mL, 2M, 30 mmol) in cyclohexane was added dropwise to a room temperature stirred suspension of triethylamine hydrochloride (0.25 g, 1.8 mmol). When the mixture became homogeneous, the solution was cooled to −78° C. in a dry-ice/acetone bath and 20 mL of anhydrous THF was added. Neat 1,3-difluorobenzene (3 mL, 30.4 mmol) was added dropwise and the solution stirred for 15 minutes. The −78° C. solution was transferred by cannula into a −78° C. solution of cyanuric chloride (5.5 g, 30 mmol) in dry THF (25 mL). The dry-ice/acetone cold bath was removed and the mixture allowed to come to room temperature. Once at room temperature the orange-red mixture was poured into 100 mL of half saturated aqueous bicarbonate solution. The mixture was allowed to stand for 15 minutes. Hexanes (100 mL) were added and after thorough mixing the organic layer was separated from the aqueous layer. The organic layer was dried over magnesium sulfate and then filtered to remove the magnesium sulfate. The solution was concentrated on a rotary evaporator to yield an oil. The oil was dissolved in a minimal amount of methylene chloride and loaded onto 100 g of silica gel. The silica gel was eluted with 10% ethyl acetate in hexanes. The organic eluent was concentrated on a rotary evaporator and the product precipitated from methylene chloride and hexane to yield 0.7 g of 2,4-dichloro-6-(2,6-difluorophenyl)-1,3,5-triazine (XXV). ESI/MS 262.0, 263.9, 265.9 (M+H).

1. stirringthe solution stirred for 15 minutes
2. customThe −78° C. solution
3. customwas transferred by cannula into a −78° C.
4. customThe dry-ice/acetone cold bath was removed
5. customto come to room temperature
6. additionOnce at room temperature the orange-red mixture was poured into 100 mL of half saturated aqueous bicarbonate solution
7. additionHexanes (100 mL) were added
8. additionafter thorough mixing the organic layer
9. customwas separated from the aqueous layer
10. dry with materialThe organic layer was dried over magnesium sulfate
11. filtrationfiltered
12. customto remove the magnesium sulfate
13. concentrationThe solution was concentrated on a rotary evaporator
14. customto yield an oil
15. washThe silica gel was eluted with 10% ethyl acetate in hexanes
16. concentrationThe organic eluent was concentrated on a rotary evaporator
17. customthe product precipitated from methylene chloride and hexane

ORD record

ord-c802f4245ae347fdb5eae030f32d3b7d

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785630B2