Nitromethane → 3-(2-Nitro-ethyl)-biphenyl

Temperature

100 °C

To a mixture of 3-phenyl-benzaldehyde (430 mg, 2.4 mmol) described in Manufacturing Example 85-1-1 and acetic acid (7 mL) were added nitromethane (0.95 mL, 18 mmol) and ammonium acetate (540 mg, 7.1 mmol), which was stirred for 2.5 hours at 100° C. The reaction mixture was cooled to room temperature, and water was added at the same temperature, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. A mixture of dimethyl sulfoxide (9.3 mL) and acetic acid (0.62 mL) was added to the resulting residue, and sodium borohydride (140 mg, 3.8 mmol) was added to the reaction mixture at room temperature while cooling appropriately. The reaction mixture was stirred for 10 minutes at the same temperature. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The resulting residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=5:1) to obtain the title compound (380 mg, 71%).

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionfollowed by extraction with ethyl acetate
3. washThe organic layer was washed with saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under a reduced pressure
6. additionA mixture of dimethyl sulfoxide (9.3 mL) and acetic acid (0.62 mL)
7. additionwas added to the reaction mixture at room temperature
8. temperaturewhile cooling appropriately
9. stirringThe reaction mixture was stirred for 10 minutes at the same temperature
10. extractionwhich was then extracted with ethyl acetate
11. washThe organic layer was washed with saturated aqueous sodium chloride
12. concentrationwas concentrated under a reduced pressure
13. customThe resulting residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=5:1)

ORD record

ord-71543a99bfa8406083790642125bd82f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2