2-Bromo-1-fluoro-4-nitrobenzene → HCID 118022659, compound

A 0.2 M solution of cyclopropyl methanol (441 uL, 5.5 mmol) in THF stirred at 0° C. under an atmosphere of nitrogen was treated with 2 equal portions of KOtBu (579 mg, 5.2 mmol). After 5 min the ice bath was removed; the mixture was stirred for 30 min at rt before resubmerging in the ice bath and cooling to 0° C. A solution of 2-bromo-1-fluoro-4-nitrobenzene (1 g, 4.5 mmol) in THF (3 mL) was added dropwise. After 20 min, the ice bath was removed and the mixture was stirred overnight. The reaction mixture was quenched with water (50 mL) and extracted with EtOAc (3×50 ml). The combined organic layers were washed brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using a gradient of EtOAc (5 to 50%) in hexanes to afford the title compound (1.07 g, 88%) as a yellow solid.

1. customAfter 5 min the ice bath was removed
2. temperaturecooling to 0° C
3. waitAfter 20 min
4. customthe ice bath was removed
5. stirringthe mixture was stirred overnight
6. customThe reaction mixture was quenched with water (50 mL)
7. extractionextracted with EtOAc (3×50 ml)
8. washThe combined organic layers were washed brine (30 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-891fd6e4d5124f45a978a81ebd9492c7

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034900B2