Acetyl bromide → HCID 86223898, compound

HRID 2387016Notes

Reaction equation

HRID 2387016 reaction equation
[C:1]([Br:4])(=O)[CH3:2].[N+](C1C=[C:12]([CH2:14][C:15]([F:18])([F:17])[F:16])[N+:11]([O-:19])=[C:10]([CH2:20][C:21]([F:24])([F:23])[F:22])[CH:9]=1)([O-])=O.[OH-].[Na+]>CC(O)=O>[Br:4][C:1]1[CH:9]=[C:10]([CH2:20][C:21]([F:22])([F:23])[F:24])[N+:11]([O-:19])=[C:12]([CH2:14][C:15]([F:16])([F:17])[F:18])[CH:2]=1

Participants

5

Reactant 3

HCID 10482Acetyl bromideHCID 14798Sodium HydroxideHCID 86223897HCID 86223897, compound

Product 1

HCID 86223898HCID 86223898, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Acetyl bromide (14 mL) was added to a solution of 4-nitro-2,6-bis-(2,2,2-trifluoro-ethyl)-pyridine 1-oxide (2.7 g, 8.9 mmol) dissolved in AcOH (25 mL). The reaction mixture was heated to 90° C. for 5 hours. The reaction was cooled to room temperature, poured into ice, made basic with NaOH pellets and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 30% EtOAc in hexanes) gave the product as a yellow oil (2.18 g, 72%). 1H NMR (400 MHz, CDCl3): δ 3.92 (t, J=10.1 Hz, 4 H), 7.59 (s, 2 H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionpoured into ice
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a red oil
  7. customPurification by flash column chromatography (0% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-343a685f429748a7a4fefae5c8b27353
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

Loading…