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

HRID 1250006노트

반응식

HRID 1250006 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4d1099398ca04c12a86d0297e07674de
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06335446B1

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