HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Bromo-2-methylaniline → 4-(Dimethylphosphoryl)-2-methylaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Bromo-2-methylaniline | HCID 11423 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | methylphosphonoylmethane | HCID 178503022 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(Dimethylphosphoryl)-2-methylaniline | HCID 67052683 | 85.4% |
Reaction Steps
To a solution of 4-bromo-2-methylaniline (0.372 g, 2.00 mmol) in 8 mL DMF was added dimethylphosphine oxide (0.171 g, 2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and potassium phosphate (0.467 g, 2.20 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150° C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-20% 7N ammonia in methanol:dichloromethane) to afford the desired product (0.313 g, 85% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09012462B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-0ac2897e575840acb557cdbe6e795ba7 |
| Source note | uspto-grants-2015_04 |