HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 1-Chloro-3-[(4-ethenylphenyl)oxy]-5-(trifluoromethyl)benzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-{[3-Chloro-5-(trifluoromethyl)phenyl]oxy}benzaldehyde | HCID 86666212 | — |
| Catalyst | Methyltriphenyliphosphonium bromide | HCID 74505 | — |
| Product | 1-Chloro-3-[(4-ethenylphenyl)oxy]-5-(trifluoromethyl)benzene | HCID 67776939 | 80% |
Reaction Steps
To a stirred suspension of 4-{[3-chloro-5-(trifluoromethyl)phenyl]oxy}benzaldehyde (3.3 g, 10.98 mmol) and methyl(triphenyl)phosphonium bromide (3.92 g, 10.98 mmol) in dry THF (30 mL) was added NaH (1.536 g, 38.4 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 2 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (2.63 g, 8.81 mmol, 80% yield) as a light green oil. LCMS: rt=4.45 min, [M+H+]=324
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637536B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-5a92caf66ccf447fac185f37a48ddeca |
| Source note | uspto-grants-2014_01 |