Methylamine → {[3-Fluoro-5-(trifluoromethyl)phenyl]methyl}(methyl)amine

Temperature

50 °C

Methylamine 33% in MeOH (1.5 mL, 46.5 mmol) was dissolved in MeOH (15 mL). The mixture was heated at 50° C. under stirring and 1-(bromomethyl)-3-fluoro-5-(trifluoromethyl)benzene (1 g, 3.88 mmol) was added. The reaction mixture was stirred at this temperature for 3 h. The solvent was removed under vacuo, then NaOH 1M (50 mL) was added and the aqueous layer was extracted with DCM (100 mL). The organic layer was dried over Na2SO4, filtered and evaporated under vacuo to give the title compound as a yellow oil (0.5 g). 1H NMR (400 MHz, CDCl3) δ ppm 7.50 (s, 1H), 7.30 (m, 2H), 7.25 (m, 1H), 3.88 (s, 2H), 2.54, (s, 3H). UPLC-MS: Rt=0.51; m/z (ES+): 208.1 [M+H]+.

1. stirringThe reaction mixture was stirred at this temperature for 3 h
2. customThe solvent was removed under vacuo
3. additionNaOH 1M (50 mL) was added
4. extractionthe aqueous layer was extracted with DCM (100 mL)
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. customevaporated under vacuo

ORD record

ord-b7c203438ecc4fc48a35369135c248b2

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181259B2