Tert-Butyl nitrite → 1-(2,4-Dibromophenoxy)-2,2,6,6-tetramethylpiperidine

HRID 1369342Notes

Reaction equation

HRID 1369342 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].N(OC(C)(C)C)=O.[Br:19][C:20]1[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:21]=1N>[Cu](F)F.N1C=CC=CC=1>[Br:19][C:20]1[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:21]=1[O:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 120042,4-DibromoanilineHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 120843011-(2,4-Dibromophenoxy)-2,2,6,6-tetramethylpiperidineYield 68.5%

Reagents, catalysts & solvents 2

HCID 522688Copper fluorideCatalystHCID 1049PyridineSolvent

Procedure

The procedure of Example 1 is repeated using 1.95 g (12.5 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 3.92 g (38 mmol) of tert-butyl nitrite, 12.5 mg (0.125 mmol) of copper(II) fluoride, 120 mL of pyridine and 6.30 g (25 mmol) of 2,4-dibromoaniline at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 3.34 g of the title compound as a light yellow oil in 68.5% yield. The structure is confirmed by 1Hnmr analysis.

Workup

  1. customat 70° C
  2. customThe crude product obtained
  3. customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-de3e3094b4734f06967ad48ff1add896
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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