Aniline → p-Allylnitrobenzene

HRID 1595019

반응식

HRID 1595019 반응식
[C:1](ON=O)(C)([CH3:3])[CH3:2].C(Br)C=C.[N+:12]([C:15]1[CH:21]=[CH:20][C:18](N)=[CH:17][CH:16]=1)([O-:14])=[O:13].NC1C=CC=CC=1>CC#N>[CH2:3]([C:18]1[CH:20]=[CH:21][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)[CH:1]=[CH2:2]

참가 물질

6

반응물 4

HCID 6115AnilineHCID 74754-NitroanilineHCID 7841Allyl bromideHCID 10906Tert-Butyl nitrite2회

생성물 1

HCID 595953p-Allylnitrobenzene수율 67.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
35 °C

실험 절차

To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (30 ml), 4-nitroaniline (414 mg, 3.0 mmol) was added during 20 minutes, while maintaining the temperature of the reaction mixture at 34-36° C. At the end of the addition of the aniline, extra t-butylnitrite (180 μl, 1.5 mmol) was added to the reaction mixture which then was stirred at 35° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) gave 330 mg of 4-allylnitrobenzene as a light yellow oil containing 15% of 4-bromonitrobenzene. This corresponds to 55% yield of 4-allylnitrobenzene. 1H NMR (CDCl3, 300 MHz) δ 8.16, (m, 2H, J=8.6 Hz), 7.35, (m, 2H, J 8.6 Hz), 6.02-5.88, (m, 1H), 5.19-5.08, (m, 2H), 3.49, (d, 2H, J=6.6 Hz).

후처리

  1. additionwas added to the reaction mixture which
  2. customThe volatile material in the reaction mixture was removed at reduced pressure

출처 및 근거

ORD 기록
ord-c8e38dc4bef7436fb086041def9ba16a
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284894B1

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