Buchwald–Hartwig amination: Bromobenzene → n-Phenylsulfanilamide
30% yield, run at 130 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Bromobenzene | C₆H₅Br | |
| Reactant | Sulfanilamide | C₆H₈N₂O₂S | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Dimethylacetamide | C₄H₉NO | |
| Product | n-Phenylsulfanilamide | C₁₂H₁₂N₂O₂S | 30% |
Conditions
- Temperature
- 130 °C
Yield
- 30% of n-Phenylsulfanilamide.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
A mixture of 4-aminobenzenesulfonamide (100 mg, 0.58 mmol), bromobenzene (0.061 mL, 0.58 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.9 mg, 0.05 mmol), diacetoxypalladium (5.21 mg, 0.02 mmol) and cesium carbonate (227 mg, 0.70 mmol) in degassed DMA (1.8 mL) was heated **_in the microwave_** for 20 min at 130 °C. LC MS FLA-04227-96-01 (pH extract 7-8) showed some product and a few bromobenzene left. Heating was continued for 15 min at 150°C. LC MS FLA-04227-96-02 (pH extract 7-8) showed reaction stalled. Reaction was stopped. Extraction with AE + ethanol / aq. sat NH4Cl (pH7), then back extraction with DCM.The organics were dried over MgSO4 and concentrated _in vacuo._ The crude product was adsorbed on silica gel 40-60µm and purified by flash chromatography on silica
The source
This record comes from experimental reaction archive (ord-2f18202487aa4ad2b8bb581b02b238ef). Open the source and check it against what is on this page.
experimental reaction archive record ord-2f18202487aa4ad2b8bb581b02b238ef from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.