1-Nitronaphthalene → 1-Bromo-5-nitronaphthalene

HRID 499976

반응식

HRID 499976 반응식
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:14]Br>>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[Br:14])([O-:3])=[O:2]

참가 물질

3

반응물 2

HCID 68491-NitronaphthaleneHCID 24408Bromine

생성물 1

HCID 2199881-Bromo-5-nitronaphthalene

반응 조건

온도
90 °C

실험 절차

A mixture of 1-nitronaphthalene (10.0 g, 58 mmol) and FeCl3 (0.066 g, 0.41 mmol) was heated to 90° C. To the solution was added dropwise bromine (3.0 mL, 58 mmol) (no any solvent was used for this reaction). The reaction mixture was stirred at 90° C. for 2 hrs. After cooling down to room temperature, the mixture was recrystallized from ethanol to give compound A as a yellow needle crystal (7.3 g, 50%). mp 119-120° C.; 1H NMR (300 MHz, CDCl3) δ 8.44 (d, J=8.7 Hz, 1H), 8.34 (d, J=8.7 Hz, 1H), 8.13 (d, J=7.5 Hz, 1H), 7.81 (d, J=7.5 Hz, 1H), 7.56 (t, J=8.1 Hz, 1H), 7.44 (t, J=8.1 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ 147.2, 133.6, 132.7, 131.8, 129.6, 126.4, 125.7, 124.6, 123.7, 123.0. EI-MS (m/z) Calcd. for C10H6BrNO2:251 (M+), Found: 251.

후처리

  1. customwas used for this reaction)
  2. temperatureAfter cooling down to room temperature
  3. customthe mixture was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-449799d254ef4363b4a889489a437346
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767817B2

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