Hydrochloric Acid → 5-Bromo-3-fluoropyridine-2-carbonitrile

HRID 1711492Notes

Reaction equation

HRID 1711492 reaction equation
S(=O)(=O)(O)O.[F-:6].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:24][C:25]1[CH:26]=[C:27]([N+]([O-])=O)[C:28]([C:31]#[N:32])=[N:29][CH:30]=1.Cl>CN(C=O)C>[Br:24][C:25]1[CH:26]=[C:27]([F:6])[C:28]([C:31]#[N:32])=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1118Sulfuric AcidHCID 2724141Tetrabutylammonium FluorideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 441966805-Bromo-3-fluoropyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-40 °C

Procedure

Sulfuric acid (0.02 eq) was added to a solution of tetrabutylammonium fluoride (3 eq) in DMF (5 vol) and the mixture cooled to −40° C. A solution of the compound of Step 2 (1 eq) in DMF (2 vol) was added maintaining the temperature <−35° C. After about 20 minutes 2N HCl (3 vol) was added followed by 1N HCl (15 vol). The precipitated product was collected by filtration to give the desired product.

Workup

  1. temperaturemaintaining the temperature <−35° C
  2. filtrationThe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-f3f2353fdef84bd5abb90042669defcd
Source dataset
uspto-grants-2010_09
Patent number
US07790754B2

Reaction notes

Loading…