Methanol → Methyl 2-bromo-5-fluoropyridine-4-carboxylate

HRID 218879Notes

Reaction equation

HRID 218879 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])=[CH:9][N:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 467392772-Bromo-5-fluoroisonicotinic acid

Product 1

HCID 46311206Methyl 2-bromo-5-fluoropyridine-4-carboxylateYield 81%

Procedure

To a solution of 2-bromo-5-fluoroisonicotinic acid (1.5 g, 6.82 mmol) in methanol (75 ml), thionyl dichloride (2.5 ml, 34.09 mmol) was added drop-wise. The reaction mixture was stirred overnight. The solvent was removed under high vacuum. The residual solid was distilled at 90° C. under vacuum to get 1.3 g (81%) of pure methyl 2-bromo-5-fluoroisonicotinate:

Workup

  1. customThe solvent was removed under high vacuum
  2. distillationThe residual solid was distilled at 90° C. under vacuum

Sources & evidence

ORD record
ord-3a5b8af830bd4450863c3ca59108a18f
Source dataset
uspto-grants-2012_06
Patent number
US08198457B2

Reaction notes

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