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

HRID 1954290Notes

Reaction equation

HRID 1954290 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.[H+].[B-:14]([F:18])([F:17])([F:16])[F:15].[N:19](OC(C)(C)C)=O>C(O)C>[F:15][B-:14]([F:18])([F:17])[F:16].[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. fluoboric 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-c4673df47347430881a5d5975a480746
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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