HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 22259691, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Cyclopropylbenzaldehyde | HCID 11506474 | — |
| Reactant | 4-Bromo-1-tert-butyl-2-chlorobenzene | HCID 59596512 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | HCID 22259691 | HCID 22259691 | 82% |
Reaction Steps
The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 4-bromo-1-tert-butyl-2-chloro-benzene (200 mg, 0.81 mmol), nBuLi (0.66 ml, 1.6M solution in hexane, 1.05 mmol) and DMF (251 μl, 3.23 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-tert-butyl-3-chloro-benzaldehyde (130 mg, 82%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 9.94 (s, 1H), 7.85 (d, J=2 Hz, 1H), 7.70 (dd, J=2 and 8 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 1.51 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07259183B2 |
| Source dataset | uspto-grants-2007_08 |
| ORD ID | ord-5041c2ae980145c2baa2c3f762bc3b54 |
| Source note | uspto-grants-2007_08 |