Tert-Butyl nitrite → 4-Bromo-2,6-diethylbenzenediazonium Tetrafluoroborate

HRID 1280921Notes

Reaction equation

HRID 1280921 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 234456594-Bromo-2,6-diethylbenzenediazonium TetrafluoroborateYield 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. 1HNR: consistent.

Workup

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

Sources & evidence

ORD record
ord-ad271916c8c34f67ab044f1b517a9e50
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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