Reaction #725867

ord-e7b9911c7bda4da2aa5eebd43269fadf

Reaction equation

CC(C)(C)c1ccc(N)cc1
4-tert-butylaniline
F[B-](F)(F)F.N#[O+]
nitrosonium tetrafluoroborate
[Br-].[K+]
KBr
→
CC(C)(C)c1ccc([N+]#N)cc1.F[B-](F)(F)F
4-tert-Butylbenzenediazonium tetrafluoroborate
Yield 78.0%

Reactants

CC(C)(C)c1ccc(N)cc1
4-tert-butylaniline
F[B-](F)(F)F.N#[O+]
nitrosonium tetrafluoroborate
[Br-].[K+]
KBr

Reagents

None

Solvents

CC#N
acetonitrile
ClCCl
methylene chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The 4-tert-butylaniline was dissolved in a 1:1 mixture of acetonitrile and dry methylene chloride prior to addition to the nitrosonium tetrafluoroborate. Yield: 78%. MP 91° C. IR (KBr) 3364.8, 3107.3, 2968.6, 2277.2, 1579.2, 1482.0, 1418.0, 1373.5, 1269.8, 1056.9, 841.1, 544.6, 621.4 cm1. 1H NMR (400 MHz, CD3CN) δ 8.16 (ABq, J=9.0 Hz, Δv=298.7 Hz, 4H), 1.30 (s, 12H). 13C NMR (100 MHz, CD3CN) δ 168.85, 133.67, 130.43, 111.88, 37.86, 30.84.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07691359B2uspto-grants-2010_04