Sodium Fluoride → 2,4,6-Trichloro-5-fluoropyrimidine

HRID 1885704Notes

Reaction equation

HRID 1885704 reaction equation
[F:1]F.[Cl:3][C:4]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[N:5]=1.[F-].[Na+]>ClC(Cl)(Cl)F>[F:1][C:7]1[C:6]([Cl:11])=[N:5][C:4]([Cl:3])=[N:9][C:8]=1[Cl:10]

Participants

5

Procedure

0.5 mol of fluorine in the form of a 30% by volume mixture with helium was introduced into a suspension of 36.7 g (0.2 mol) of 2,4,6-trichloropyrimidine, 21 g of sodium fluoride (0.5 mol) and 250 ml of trichlorofluoromethane, at a temperature of -78° C. The rate of introduction was 0.15 mol of fluorine per hour. After the introduction, the reaction mixture was filtered and 19.3 g of pure 5-fluoro-2,4,6-trichloropyrimidine were obtained from the filtrate by distillation over iron filings. This corresponds to a yield of 48% of theory. The boiling point of the isolated product was 80°-87° C. at 10 mbar. The reaction mixture also contained more highly fluorinated pyrimidine derivatives.

Workup

  1. filtrationAfter the introduction, the reaction mixture was filtered

Sources & evidence

ORD record
ord-d0b214783d1d42c189fbe9d14cd04a5e
Source dataset
uspto-grants-1992_09
Patent number
US05145961

Reaction notes

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