Allyl bromide → HCID 69979367, compound

HRID 1595005Notes

Reaction equation

HRID 1595005 reaction equation
[C:1]([O:5]N=O)([CH3:4])([CH3:3])C.[CH2:8](Br)[CH:9]=[CH2:10].CC#N.C([C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([N+:25]([O-:27])=[O:26])C=1)N)(=O)C>>[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[C:19]([CH2:20][CH:22]=[CH:23][N+:25]([O-:27])=[O:26])[CH:18]=1)(=[O:5])[CH3:4]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 10906Tert-Butyl nitriteHCID 86757346HCID 86757346, compound

Product 1

HCID 69979367HCID 69979367, compound

Procedure

To a solution of t-butylnitrite (0.24 ml, 2.1 mmol) and allylbromide (1.8 ml, 25.2 mmol) in 3 ml CH3CN 3-acetyl-5-nitroaniline (0.25 g, 1.4 mmol) was added, so that the temperature was maintained between 20 and 25° C., and the mixture was stirred for 10 min at room temperature. The volatile material in the reaction solution was then removed at reduced pressure to give 3-acetyl-5-nitroallylbenzene. 1H-NMR (CDCl3, 300 MHz) δ ppm: 8.61 (s, 1H), 8.25 (s, 1H), 8.10 (s, 1H), 6.03-5.88 (m, 1H), 5.23-5.11 (m, 2H), 3.55 (d, 2H).

Workup

  1. temperaturewas maintained between 20 and 25° C.
  2. customThe volatile material in the reaction solution was then removed at reduced pressure

Sources & evidence

ORD record
ord-6bf652f1bda14f29bf72bcc1e1c1c51d
Source dataset
uspto-grants-2001_09
Patent number
US06284894B1

Reaction notes

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