Buchwald–Hartwig amination: 1-Chloro-4-(trifluoromethyl)benzene → Methyl 2-methyl-2-[4-(trifluoromethyl)anilino]propanoate
0% yield, run at 180 °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 | 1-Chloro-4-(trifluoromethyl)benzene | C₇H₄ClF₃ | |
| Reactant | Methyl 2-amino-2-methylpropanoate | C₅H₁₁NO₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Bis(adamantan-1-yl)(butyl)phosphane | C₂₄H₃₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | (Trifluoromethyl)benzene | C₇H₅F₃ | |
| Product | Methyl 2-methyl-2-[4-(trifluoromethyl)anilino]propanoate | C₁₂H₁₄F₃NO₂ | 0% |
Conditions
- Temperature
- 180 °C
Yield
- 0% of Methyl 2-methyl-2-[4-(trifluoromethyl)anilino]propanoate.
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.
- Methyl 2-(4-methoxyanilino)-2-methylpropanoate0%
- Methyl 2-methyl-2-[(4-methylphenyl)amino]propanoate0%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline46%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline45%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline45%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline43%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline42%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline40%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline37%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline35%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline35%
- 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline34%
Procedure
Copied from the source record, unedited
1-chloro-4-(trifluoromethyl)benzene (0.068 mL, 0.51 mmol), methyl 2-amino-2-methylpropanoate (0.05 g, 0.43 mmol),BUTYLDI-1-ADAMANTYLPHOSPHINE (0.015 g, 0.04 mmol), sodium 2-methylpropan-2-olate (0.082 g, 0.85 mmol) and diacetoxypalladium (4.79 mg, 0.02 mmol) was added to a microwave vial. (TRIFLUOROMETHYL)-BENZENE (0.5 mL) was used as solvent, before use the solvent was bubbled with nitrogen (1-1.2 mL/mmol amine). The mixture was bubbled with nitrogen before the vial was sealed. The mixture was heated in microwave at 180° for 60min.. The mixture was heated in microwave at 180° for 60min. No conversion of startingmaterial was observed.
The source
This record comes from experimental reaction archive (ord-d712f5c0551541748b4f06a98eb63af5). Open the source and check it against what is on this page.
experimental reaction archive record ord-d712f5c0551541748b4f06a98eb63af5 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
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