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

HRID 1250006Notes

Reaction equation

HRID 1250006 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4d1099398ca04c12a86d0297e07674de
Source dataset
uspto-grants-2002_01
Patent number
US06335446B1

Reaction notes

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