Tert-Butyl nitrite → HCID 10868638, compound

HRID 1595022Notes

Reaction equation

C(ON=O)(C)(C)C.Br[CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]1.[N+:15]([C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=1)N)([O-:17])=[O:16]>CC#N>[N+:15]([C:18]1[CH:19]=[C:20]([CH:14]2[CH2:13][CH2:12][CH2:11][CH:10]=[CH:9]2)[CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 26.5 °C

Procedure

To a solution of t-butylnitrite (119 μl, 1.0 mmol) and 3-bromocyclohexene (860 μl, 7.5 mmol) in CH3CN (0.5 ml), 3,5-dinitroaniline (92 mg, 0.5 mmol) was added during 10 minutes, while maintaining the temperature of the reaction mixture at 23-30° C. After stirring for one hour at room temperature the volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) followed by preparative HPLC gave 15 mg (12%) of 3-(3,5-dinitrophenyl)cyclohexene as bright yellow crystals. 1H NMR (CDCl3, 300 MHz) δ 8.90, (t, 1H, J=2.1 Hz), 8.42, (d, 2H, J=2.1 Hz), 6.19-6.06, (m, 1H), 5.74-5.66, (m, 1H), 3.67, (m, 1H), 2.25-2.07, (m, 3H), 1.80-1.51, (m, 3H).

Workup

customwas removed at reduced pressure

Sources & evidence

ORD record: ord-e57f73146b1f4097bd40cb737bd66aea
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284894B1

Reaction notes

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