Sodium Bromide → HCID 21079532, compound

Participants

Reaction Conditions

Reaction Steps

10% aq. NaOCl (900 mL) was added dropwise to a stirred mixture of NaBr (30.9 g, 0.30 mol), NaHCO3 (50.4 g, 0.60 mol), water (200 mL) and a solution of 1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanol (80.0 g from Example 1) and TEMPO (0.94 g, 6 mmol) in CH2Cl2 (100 mL) at 0 to 5° C. The mixture was stirred for 0.5 h at the same temperature and 10% aq. Na2S2O3.5H2O (150 mL) was added. The aqueous layer was separated and extracted with CH2Cl2. The combined organic layer was dried over Na2SO4, filtered trough thin layer of silica gel and concentrated in vacuo. A mixture of the residue and hexane (300 mL) was stirred for 1 h at rt and for 1 h at 0 to 5° C. The precipitate was filtered, washed on the filter with cold hexane and dried in vacuo to give 60.5 g of 1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanone as off-white crystals: mp 38–39° C. 1H NMR (CDCl3) δ: 7.41 (t, J=8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 7.13 (s, 1H), 7.0 (d, J=8.0 Hz, 1H), 4.82 (s, 2H), 4.37 (s, 2H).

Provenance & Evidence