Bromobenzene → Phosphonic acid, phenyl-, diethyl ester

Temperature

80 °C

In a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar was charged with palladium(II) acetate (1.4 mg, 0.00637 mmol, 0.02 equivalents), 8-(1,1′-binaphthyl-2-yl)-7,7,9,9-tetramethyl-1,4-dioxa-8-phosphaspiro[4.5]decane (3.6 mg, 0.00764 mmol, 0.024 equivalents) and ethanol (0.64 mL). To the slurry were added triethylamine (67 μL, 0.478 mmol, 1.5 equivalents), bromobenzene (34 μL, 0.318 mmol, 1 equivalent) and diethylphosphite (49 μL, 0.382 mmol, 1.2 equivalents). The vial was sealed with a crimp top and stirred at 80° C. After 24 hours, the vial was removed from the heating block, cooled to room temperature and brought out of the glovebox. The reaction solution was diluted with tetrahydrofuran (2 mL) and filtered into a tared 125-mL Erlenmeyer flask. The vial was rinsed with tetrahydrofuran (5×1 mL), followed by washing of the filter cake with tetrahydrofuran (5 mL). A wt % analysis was performed on the filtrate and an assay yield of 59% was measured versus commercially available diethyl phenylphosphonate.

1. customIn a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar
2. customThe vial was sealed with a crimp top
3. customthe vial was removed from the heating block
4. temperaturecooled to room temperature
5. additionThe reaction solution was diluted with tetrahydrofuran (2 mL)
6. filtrationfiltered into a tared 125-mL Erlenmeyer flask
7. washThe vial was rinsed with tetrahydrofuran (5×1 mL)
8. washby washing of the filter cake with tetrahydrofuran (5 mL)

ORD record

ord-2357e0da1d7a4fd9abeb5769e85d37d1

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975443B2