Sodium Bromide → HCID 21079532, compound

Temperature

2.5 °C

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).

1. customat 0 to 5° C
2. additionwas added
3. customThe aqueous layer was separated
4. extractionextracted with CH2Cl2
5. dry with materialThe combined organic layer was dried over Na2SO4
6. filtrationfiltered trough thin layer of silica gel
7. concentrationconcentrated in vacuo
8. additionA mixture of the residue and hexane (300 mL)
9. filtrationThe precipitate was filtered
10. washwashed on the
11. filtrationfilter with cold hexane
12. customdried in vacuo

ORD record

ord-1c767922db0045f1bbf5bf81312875dc

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166730B2