HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromine → 1-Tetralone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bromine | HCID 24408 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 1-(3-Methoxyphenyl)propan-2-ol | HCID 12499852 | — |
| Reactant | 6-(Methyloxy)-3-(3,3,3-trifluoropropyl)-3,4-dihydro-1(2H)-naphthalenone | HCID 68536263 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-Tetralone | HCID 10724 | — |
| Product | 2-Bromo-6-(methyloxy)-3-(3,3,3-trifluoropropyl)-1-naphthalenol | HCID 68536262 | — |
Reaction Steps
Treatment of 6-(methyloxy)-3-(3,3,3-trifluoropropyl)-3,4-dihydro-1(2H-naphthalenone (121) (0.40 g, 1.47 mmol) with bromine followed by DBU in CH3CN gave 0.47 g (92% from tetralone) of the title compound (122) as a white solid. 1H NMR (400 MHz, CDCl3): δ 2.40-2.55 (m, 2H), 3.05-3.10 (m, 2H), 3.91 (s, 3H), 6.06 (s, 1H), 7.02 (d, J=2.5 Hz, 1H), 7.12 (dd, J1=9.1 Hz, J2=2.5 Hz, 1H), 7.20 (s, 1H), 8.10 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 347 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07649093B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-4a729947566148e19eedce03efc65f05 |
| Source note | uspto-grants-2010_01 |