Triethylamine → HCID 22632168, compound

HRID 2416698Notes

Reaction equation

HRID 2416698 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10]Br.[F:12][C:13]([F:23])([F:22])[C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.C(N(CC)CC)C>CS(C)=O.C1COCC1>[F:12][C:13]([F:22])([F:23])[C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][CH2:10][C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[Br:1])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 768044-(Trifluoromethyl)benzylamineHCID 35259512-Bromo-5-methoxybenzyl bromide

Product 1

HCID 22632168HCID 22632168, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-bromo-3-bromomethylanisole (35 g, 125 mmol) in anhydrous DMSO (50 mL) and dry THF (50 mL) was added 4-trifluoromethylbenzylamine (30 g, 171 mmol) followed by triethylamine (18 mL, 129 mmol). After stirring for 18 h at RT the reaction was concentrated, diluted with aqueous 1 N NaOH (250 mL) and extracted with Et2O (2×250 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to dryness. The residue which remained was purified by flash chromatography on silica gel (10 to 20% EtOAc/CHCl3) to give the title compound (34.17 g, 73%): TLC (20% EtOAc/CHCl3) Rf 0.63; 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J=8.2 Hz, 2H), 7.49 (d, J=8.2 Hz, 2H), 7.43 (d, J=8.6 Hz, 1H), 6.96 (d, J=3.1 Hz, 1H), 6.70 (dd, 1H), 3.86 (s, 2H), 3.84 (s, 2H), 3.79 (s, 3H), 1.75 (br s, 1H).

Workup

  1. concentrationwas concentrated
  2. additiondiluted with aqueous 1 N NaOH (250 mL)
  3. extractionextracted with Et2O (2×250 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customThe residue which remained was purified by flash chromatography on silica gel (10 to 20% EtOAc/CHCl3)

Sources & evidence

ORD record
ord-2d7cc7ab4323485bba24b7bad02a01f2
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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