Bromine → HCID 86662700, compound

HRID 473169Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O-:11])=[O:10])=[N:6][CH:7]=1.[Na+].BrBr.P(Br)(Br)[Br:16]>>[Br:16][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1)[C:9]([OH:11])=[O:10]

Participants

Reactant 3

HCID 24408Bromine

HCID 24614Phosphorus tribromide

HCID 66609994HCID 66609994, compound

Product 1

HCID 86662700HCID 86662700, compound

Procedure

Sodium 2-(5-fluoropyridin-2-yl)acetate is treated with 1-1.5 equiv of Br2 in the presence of phosphorus tribromide under standard Hell-Volhard-Zelinskii reaction conditions (J. March “Advanced Organic Chemistry” 3rd Edition, 1985, p. 531 and references therein) to afford 2-bromo-2-(5-fluoropyridin-2-yl)acetic acid.

Sources & evidence

ORD record: ord-a3a5e3e59d344f90935b5221889700e5
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633207B2

Reaction notes

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