4-Chlorobenzophenone → Methanone, (4-nitrophenyl)phenyl-

In a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar was charged with 4-chlorobenzophenone (100 mg, 0.462 mmol, 1 equivalent), sodium nitrite (63.7 mg, 0.923 mmol, 2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.005 or 0.0025 equivalents) and 7,7,9,9-tetramethyl-8-(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)-1,4-dioxa-8-phosphaspiro[4.5]decane (0.012 or 0.006 equivalents, respectively). The solids were slurried in t-butyl alcohol (0.84 mL) before adding tris[2-(2-methoxyethoxy)ethyl]amine (TDA-1) (7.4 μL, 0.023 mmol, 0.05 equivalents). The vial was sealed with a crimp top and placed in a heating block at 130° C. After indicated reaction time, the vial was cooled to room temperature and brought out of the glovebox. The reaction solution was diluted with tetrahydrofuran (2 mL) and filtered through a pad of diatomaceous earth into a tared 125-mL Erlenmeyer flask. The vial was rinsed with tetrahydrofuran (5×1 mL) before the filter cake was washed with tetrahydrofuran (5 mL). A wt % analysis was performed on the filtrate and an assay yield was measured.

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. customplaced in a heating block at 130° C
4. customreaction time
5. filtrationfiltered through a pad of diatomaceous earth into a tared 125-mL Erlenmeyer flask
6. washThe vial was rinsed with tetrahydrofuran (5×1 mL) before the filter cake
7. washwas washed with tetrahydrofuran (5 mL)
8. customan assay yield

ORDレコード

ord-73657a4518c24570a6c0d55211b56a6a

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08841487B2