2,4-Difluoronitrobenzene → N-(1-(3-bromophenyl)ethyl)-5-fluoro-2-nitrobenzenamine

HRID 2426004

반응식

HRID 2426004 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.F[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[CH3:9])[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 167857641-(3-Bromophenyl)ethanamine

생성물 1

HCID 58707271N-(1-(3-bromophenyl)ethyl)-5-fluoro-2-nitrobenzenamine수율 74%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1-(3-bromophenyl)ethanamine (1.0 g, 5.0 mmol), 2,4-difluoro-1-nitrobenzene (0.8 g, 5.0 mmol), N,N-diisopropylethylamine (1.7 mL, 10.0 mmol) and acetonitrile (20 mL) was stirred for 18 h and concentrated in vacuo. The residue was dissolved in ethyl acetate; this solution was washed with water, dried over Na2SO4 and concentrated in vacuo to yield the title compounds as a yellow oil (1.25 g, 74%). 1H NMR (400 MHz, CDCl3): δ 8.51 (d, 1H), 8.25 (m, 1H), 7.48 (s, 1H), 7.41 (m, 1H), 7.25 (m, 2H), 6.36 (m, 1H), 6.24 (m, 1H), 4.55 (m, 1H), 1.63 (d, 3H). MS (ESI) m/z: Calculated: 338; Observed: 339 (M+H+).

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthis solution was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c3dd266b258e453d8e9a861f619ed49c
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968538B2

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