Potassium Carbonate → [3,5-Bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)amine

HRID 17039

反応式

HRID 17039 の反応式
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[Br:16])(=O)=O.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:22][NH2:23].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCCC>CN(C=O)C.O>[F:17][C:18]([F:31])([F:32])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[CH2:22][NH:23][CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[Br:16]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 21226206Ethyl acetate hexaneHCID 866153922-Bromo-5-nitrobenzyl methanesulfonate

生成物 1

HCID 86615393[3,5-Bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-bromo-5-nitrobenzyl methanesulfonate from Step B (0.42 g, 1.35 mmol) and 3,5-bis-trifluoromethyl benzylamine (0.33 g, 1.35 mmol) in DMF (10 ml) at 0° C., potassium carbonate (0.37 g, 2.69 mmol) was added. The mixture was stirred at 0° C. for 2 h. TLC analysis (EtOAc/hexane=2:8) showed completion of the reaction. Water (50 ml) was added. The mixture was extracted with EtOAc (3×40 ml). The combined organic layers were washed with brine, and dried over sodium sulfate. The title compound was obtained by flash column chromatography using 2:8 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 8.35 (d, J=2.5 Hz, 1H), 8.03 (dd, J=8.5, 2.5 Hz, 1H), 7.88 (s, 2H), 7.81 (s, 1H), 8.76 (d, J=8.5 Hz, 1H), 4.00 (s, 4H).

後処理

  1. customcompletion of the reaction
  2. extractionThe mixture was extracted with EtOAc (3×40 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-01c64f527dae46e1bfa7b838e4d4470f
出典データセット
uspto-grants-2010_06
特許番号
US07737295B2

関連ノート

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