Acetyl bromide → HCID 86223898, compound

HRID 859625Notes

Reaction equation

HRID 859625 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-24685af02a7548f3ac7bcbbf7335a9a8
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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