Sulfuric Acid → 3-Bromo-4-chloro-5-fluoro-2-picoline

HRID 1080202Notes

Reaction equation

HRID 1080202 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([CH3:9])[CH:3]=1.[Br:10]Br.S(=O)(=O)(O)O>>[Br:10][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[C:7]([F:8])[C:2]=1[Cl:1]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 196914104-Chloro-5-fluoro-2-methylpyridine

Product 1

HCID 196914363-Bromo-4-chloro-5-fluoro-2-picoline

Procedure

4-Chloro-5-fluoro-2-picoline, the product of Exmnple 66, is treated with bromine in fuming sulfuric acid containing 65% sulfur trioxide for 7 hours at 80° C. as described by L. van der Does and H. J. Hertog in Rec Tray Chim 81:864 (1965) to afford the title compound.

Workup

  1. customfor 7 hours
  2. customat 80° C.

Sources & evidence

ORD record
ord-238cbc52e1804f11bf7513557d638f13
Source dataset
uspto-grants-1996_12
Patent number
US05580872

Reaction notes

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