Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 4-Bromo-2-(1,1-dimethylethyl)-N,N-diethylbenzenamine | HCID 66671963 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86042697 | HCID 86042697 | 102.2% |
Reaction Steps
3.6 g (13 mmol) of (4-bromo-2-tert-butylphenyl)-diethylamine are diluted in 100 ml of THF, under a stream of nitrogen. The medium is cooled to −78° C. and then 7.8 ml (20 mmol) of a 2.5M solution of nBuLi are added. After stirring for 45 minutes, 1.5 ml (20 mmol) of DMF are added and the solution is brought back to ambient temperature. After 15 minutes, the mixture is poured into a saturated solution of ammonium chloride and then extracted twice with ethyl acetate. The organic phase is dried over sodium sulphate and then concentrated to dryness. 3.1 g of 3-tert-butyl-4-diethylaminobenzaldehyde are obtained in the form of a yellow oil (yield=100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163952B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-fb66f79ea88d45e2a2f2498efbdd22a7 |
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| Source note | uspto-grants-2012_04 |
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