Water → Benzenamine, 2-bromo-6-ethynyl-4-(trifluoromethyl)-

HRID 855282ノート

反応式

HRID 855282 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]#[C:13][Si](C)(C)C)[C:3]=1[NH2:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]#[CH:13])[C:3]=1[NH2:18]

参加物

5

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 693432912-Bromo-4-(trifluoromethyl)-6-[2-(trimethylsilyl)ethynyl]benzenamine

生成物 1

HCID 86093740Benzenamine, 2-bromo-6-ethynyl-4-(trifluoromethyl)-収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

4.26 g of 2-bromo-4-trifluoromethyl-6-trimethylsilanylethynyl-phenylamine (13 mmol) were dissolved in 40 ml THF and the solution was cooled to 0° C. Then 15.2 ml of a 1 M solution of tetrabutylammonium fluoride in THF (15 mmol) were added and the reaction mixture was stirred for 20 min at 0° C. After addition of water, the mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried with magnesium sulfate, filtered and concentrated. 1.82 g (54%) of 2-bromo-6-ethynyl-4-trifluoromethyl-phenylamine were isolated as a brown solid after purification (silica gel; cyclohexane/EtOAc 9:1). 1H NMR (CDCl3, 300 MHz): δ 3.48 (s, 1H), 5.03 (br s, 2H), 7.54 (s, 1H), 7.65 (s, 1H).

後処理

  1. extractionthe mixture was extracted with EtOAc
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-41551fb44a914313a186e6367bf40500
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

反応ノート

読み込み中…