Potassium Carbonate → HCID 118093821, compound

A solution of 2-amino-4-bromo-3-phenoxyphenol (0.060 g, 0.214 mmol) in acetonitrile (3.88 mL) and water (1.21 mL) was treated with potassium carbonate (0.118 g, 0.857 mmol), followed by the addition of bromoacetyl bromide (0.0279 mL, 0.321 mmol), and the resultant reaction mixture was stirred at RT for 30 min, after which time additional bromoacetyl bromide (0.0186 mL, 0.214 mmol) was added dropwise and the reaction mixture was stirred at RT for 1 h, then warmed to 75° C. and stirred at that temperature for 30 min. The reaction mixture was concentrated and diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo the yield a crude product. Purification by flash column chromatography (100% hexanes to 50% EtOAc/hexanes) gave the desired product (59.5 mg, 87%) as a white solid. LCMS calculated for C14H11BrNO3 (M+H)+: m/z=320.0, 322.0. found: 319.9, 321.9.

1. customthe resultant reaction mixture
2. stirringthe reaction mixture was stirred at RT for 1 h
3. temperaturewarmed to 75° C.
4. stirringstirred at that temperature for 30 min
5. concentrationThe reaction mixture was concentrated
6. additiondiluted with ethyl acetate and water
7. customLayers were separated
8. washthe organic layer was washed with brine
9. dry with materialdried with sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo the
12. customyield a crude product
13. customPurification by flash column chromatography (100% hexanes to 50% EtOAc/hexanes)

ORD record

ord-0c193a9290e44ca78553e10ebb9c4f4b

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399640B2