Ethanamine, 2,2,2-trifluoro- → HCID 11098529, compound

HRID 2416704Notes

Reaction equation

HRID 2416704 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH2:16]Br>CS(C)=O>[F:1][C:2]([F:6])([F:5])[CH2:3][NH:4][CH2:16][C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[Br:7]

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 35259512-Bromo-5-methoxybenzyl bromide

Product 1

HCID 11098529HCID 11098529, compoundYield 115.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
32.5 °C

Procedure

2,2,2-Trifluoroethylamine (24 g, 242 mmol) was added rapidly to a stirred solution of 4-bromo-3-bromomethylanisole (33.6 g, 120 mmol) in anhydrous DMSO (125 mL) at RT. The reaction warmed to approximately 30-35° C. After stirring for 18 hr, the reaction was diluted with ice-cold 1 N NaOH (200 mL) and extracted with Et2O (2×300 mL). The combined organic layers were washed with brine (300 mL), dried (MgSO4), and concentrated to give the title compound (41.35 g, 96%) as a pale yellow oil: TLC (toluene) Rf 0.32; 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=9 Hz, 1H), 6.97 (d, J=3 Hz, 1H), 6.71 (dd, 1H), 3.93 (br s, 2H), 3.80 (s, 3H), 3.18 (m, 2H), 1.86 (br s, 1H).

Workup

  1. extractionextracted with Et2O (2×300 mL)
  2. washThe combined organic layers were washed with brine (300 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bd1c023b4b2c4b298b5099c01f93a99f
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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