Sodium Bicarbonate → (2-Bromo-6-(trifluoromethyl)phenyl)methanol

Participants

Reaction Steps

To 1-bromo-2-(bromomethyl)-3-(trifluoromethyl)benzene (CXXVIII) (7.51 g, 23.62 mmol) was added an aqueous saturated solution of NaHCO3 (400 mL). The reaction mixture was vigorously stirred and refluxed overnight. The reaction mixture consisted of an upper aqueous layer and a bottom oily layer, which solidified in an ice bath. The water layer was decanted and the solid was dissolved in EtOAc, dried over anhydrous MgSO4, filtrated and evaporated to dryness to give (2-bromo-6-(trifluoromethyl)phenyl)methanol (CXXIX) as an orange oil (5.49 g, 23.16 mmol, 98%). 1H NMR (DMSO-d6) δ ppm 4.67 (d, J=4 Hz, 2H), 5.23 (t, J=5 Hz, 1H), 7.43 (dd, J=8 Hz, J=8 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H); 19F NMR (DMSO-d6) δ ppm −56.33 (s, 3F); ESIMS found for C8H6BrF3O m/z 237.3 (M+H).

Provenance & Evidence