Decanal → 4-Bromo-N-decyl-3-(trifluoromethyl)aniline

HRID 1250006

反応式

HRID 1250006 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Br:24])[NH2:20].[CH:27](=O)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CO>[CH2:27]([NH:20][C:19]1[CH:21]=[CH:22][C:23]([Br:24])=[C:17]([C:16]([F:15])([F:25])[F:26])[CH:18]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

参加物

5

反応物 3

HCID 8175DecanalHCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 183293104-Bromo-N-decyl-3-(trifluoromethyl)aniline収率 53%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium triacetoxyborohydride (4 g) was added to a solution of 3-trifluoromethyl-4-bromoaniline (1.5 g) and decanal (4 mL) in methanol (90 mL). After stirring for 1 h the solution was partitioned between water and petroleum ether. The organic extract was concentrated under reduced pressure and the residue was purified via flash column chromatography using petroleum ether as eluent to give N-Decyl-4-broma-3-trifluoromethylaniline (4) (1.2 g, 53%). 1H NMR (CDCl3) δ 7.44 (d, 1H, ArH); 6.92 (d, 1H, ArH); 6.61 (dd, 1H, ArH); 3.11 (t, 2H, NCH2); 0.80 (t, 3H, CH2CH3). TLC (silica gel): Rf=0.35 (petroleum ether).

後処理

  1. customwas partitioned between water and petroleum ether
  2. extractionThe organic extract
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was purified via flash column chromatography

出典と根拠

ORDレコード
ord-4d1099398ca04c12a86d0297e07674de
出典データセット
uspto-grants-2002_01
特許番号
US06335446B1

関連ノート

読み込み中…