HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 58483266, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | Ethyl 2-chloro-6-fluorobenzoate | HCID 43389523 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58483266 | HCID 58483266 | 35.1% |
Reaction Steps
To a cold solution of ethyl 2-chloro-6-fluorobenzoate (0.500 g, 24.7 mmol) in THF (35 mL) was added LDA (6.6 g, 61.8 mmol) at −78° C. The reaction mixture was stirred for 2 h at same temperature, followed by addition of DMF (2.7 g, 37 mmol). The reaction mixture was further stirred for 2 h at same temperature. The reaction mass was quenched in dilute HCl, extracted with ethyl acetate and concentrated to afford crude product which was further purified by column chromatography eluting with EtOAC: pet. ether to afford 2.00 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 1.31 (t, 3H), 4.42 (q, 2H), 7.94-7.99 (m, 2H), 10.14 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09439890B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-4336002c571f4c5ba013cf5fcdb4679f |
| Source note | uspto-grants-2016_09 |