Iodoethane → HCID 58424902, compound

3-Methoxy-5-nitrobenzoic acid (10 g, 50.7 mmol) prepared in step 1 of Example 72 was dissolved in dichloromethane (200 ml), added with 1 M boron tribromide dichloromethane solution. The reaction mixture was stirred at room temperature for 8 hours. The mixture was poured into ice water and washed with dichloromethane. The water layer was concentrated under reduced pressure and dried in vacuo. The residue was dissolved in N,N-dimethylformamide (150 ml), added dropwise with potassium carbonate (42 g, 304 mmol) and iodoethane (20.2 ml, 253 mmol). The mixture was then stirred for one day at 60° C. and poured into ice water. The solution was extracted with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (8.49 g, yield: 70%, yellow solid).

1. washwashed with dichloromethane
2. concentrationThe water layer was concentrated under reduced pressure
3. customdried in vacuo
4. dissolutionThe residue was dissolved in N,N-dimethylformamide (150 ml)
5. stirringThe mixture was then stirred for one day at 60° C.
6. extractionThe solution was extracted with ethyl acetate
7. washwashed with brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe solvent was removed under reduced pressure
10. customthe residue was purified by flash column chromatography (hexane:ethyl acetate=5:1)

ORD record

ord-cc9b5b1db979426bb61dca8c782d5947

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815891B2