N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → [2-(4-Bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine

HRID 222470

反応式

HRID 222470 の反応式
C(O[CH:5](OC(C)C)[N:6]([CH3:8])[CH3:7])(C)C.[Br:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]([CH3:23])=[CH:16][C:15]=1[F:24]>CN(C=O)C>[Br:13][C:14]1[C:15]([F:24])=[CH:16][C:17]([CH:23]=[CH:5][N:6]([CH3:7])[CH3:8])=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1

参加物

4

反応物 2

HCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amineHCID 27793654-Bromo-5-fluoro-2-nitrotoluene

生成物 1

HCID 73878710[2-(4-Bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
125 °C

実験手順

A mixture of N,N-dimethylformamide diisopropyl acetal (1.32 mL, 6.31 mmol) and 1-bromo-2-fluoro-4-methyl-5-nitro-benzene (1.23 g, 5.26 mmol) in dry DMF (15.0 mL) was stirred at 125° C. for 3 h. The resulting mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was washed with hexane to give [2-(4-bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine as dark red solid (1.89 mg, 83%). 1H NMR (CDCl3, 400 MHz): 2.92 (s, 6H), 5.88 (d, J=12.3 Hz, 1H), 6.98 (d, J=13.2 Hz, 1H), 7.11 (d, J=10.8 Hz, 1H), 8.10 (d, J=6.9 Hz, 1H).

後処理

  1. customThe resulting mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with hexane

出典と根拠

ORDレコード
ord-1b9b703a6db84966ac7373889bb196cb
出典データセット
uspto-grants-2012_06
特許番号
US08207216B2

関連ノート

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