Tert-Butyl nitrite → HCID 23445659, compound

HRID 1067358Notes

Reaction equation

HRID 1067358 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH2:9][CH3:10])[C:5]([NH2:6])=[C:4]([CH2:11][CH3:12])[CH:3]=1.[F:13][B-:14]([F:17])([F:16])[F:15].[H+].[N:19](OC(C)(C)C)=O>C(O)C>[F:13][B-:14]([F:17])([F:16])[F:15].[Br:1][C:2]1[CH:8]=[C:7]([CH2:9][CH3:10])[C:5]([N+:6]#[N:19])=[C:4]([CH2:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 28118Tetrafluoroboric acidHCID 6114524-Bromo-2,6-diethylaniline

Product 1

HCID 23445659HCID 23445659, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At 0° C., to a stirred solution of commercial 4-bromo-2,6-diethylaniline (10.0 g, 43.9 mmol) in absolute ethanol (219 mL) was added 48% aq. tetrafluoroboric acid (17.2 mL), followed by tert-butyl nitrite (5.7 mL, 48.0 mmol). After 0.5 h, the reaction was poured into ice cold ether (877 mL). The resulting precipitate was washed with cold ether and dried to give 9.39 g (66%) of the title compound. 1H NMR: consistent.

Workup

  1. washThe resulting precipitate was washed with cold ether
  2. customdried

Sources & evidence

ORD record
ord-b8e222e004b5461f856955c16ca5661e
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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