Buchwald–Hartwig amination: 1-(Benzyloxy)-4-bromo-2-fluorobenzene → 4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-fluoroaniline
54% yield, run at 120 °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-(Benzyloxy)-4-bromo-2-fluorobenzene | C₁₃H₁₀BrFO | |
| Reactant | (2-Aminoethoxy)(tert-butyl)dimethylsilane | C₈H₂₁NOSi | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-fluoroaniline | C₂₁H₃₀FNO₂Si | 54.2% |
Conditions
- Temperature
- 120 °C
Yield
- 54% of 4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-fluoroaniline.
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
PdOAc2 (0.399 g, 1.78 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.848 g, 1.78 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (5.00 g, 17.79 mmol), 2-(tert- butyldimethylsilyloxy)ethanamine (4.16 g, 17.79 mmol) and cesium carbonate (8.69 g, 26.68 mmol) in toluene (100 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 10 hours in the microwave reactor and cooled to RT. **** _Split into 5 x 20 ml mw vials such as in each was:_ PdOAc2 (0.080 g, 0.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.170 g, 0.36 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1.000 g, 3.56 mmol), 2-(tert- butyl
The source
This record comes from experimental reaction archive (ord-fd407bedbf534487940a2a1f79aacfca). Open the source and check it against what is on this page.
experimental reaction archive record ord-fd407bedbf534487940a2a1f79aacfca 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.
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