Bromine → 2-Bromo-5-nitro-3-(trifluoromethyl)pyridine

HRID 1051130Notes

Reaction equation

HRID 1051130 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:7](=O)[NH:8][CH:9]=1)([O-:3])=[O:2].P(Br)(Br)([Br:17])=O.P(Br)(Br)Br.BrBr>>[Br:17][C:7]1[C:6]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1

Participants

5

Reactant 4

HCID 24408BromineHCID 24613Phosphorus oxybromideHCID 24614Phosphorus tribromideHCID 27750952-Hydroxy-5-nitro-3-(trifluoromethyl)pyridine

Product 1

HCID 534863502-Bromo-5-nitro-3-(trifluoromethyl)pyridineYield 88%

Conditions

Temperature
100 °C

Procedure

A mixture of 5-nitro-3-(trifluoromethyl)pyridin-2(1H)-one 3, POBr3 (1.5 equivalents), PBr3 (4 equivalents), and Br2 (2 equivalents) is heated to about 90-110° C. and is then poured into ice water. The mixture is neutralized and extracted. The combined organic phases are dried over Na2SO4 and all solvents removed under reduced pressure to obtain 2-bromo-5-nitro-3-(trifluoromethyl)pyridine 21 in a yield of 88%.

Workup

  1. extractionextracted
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. customall solvents removed under reduced pressure

Sources & evidence

ORD record
ord-58f0b7b2d984415dbfced4953acf20dd
Source dataset
uspto-grants-2016_07
Patent number
US09388159B2

Reaction notes

Loading…