HuagongsheHuagongshe Chemistry Print Report · For research reference only
Boron trifluoride etherate → 2-(5-Bromo-2-chlorobenzyl)-1-benzothiophene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-Benzothien-2-yl(5-bromo-2-chlorophenyl)methanol | HCID 23103383 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | 2-(5-Bromo-2-chlorobenzyl)-1-benzothiophene | HCID 58178458 | 56.6% |
Reaction Steps
Then, Et3SiH (9.2 mL, 0.058 mol) and BF3.Et2O (3.6 mL, 0.029 mol) were added sequentially to a chloroform (110 mL) solution of (1-benzothien-2-yl)(5-bromo-2-chlorophenyl)methanol (10.2 g, 0.0288 mol) at −15° C. The reaction mixture was warmed to room temperature and stirred at the temperature for ten hours. After the reaction mixture was added with a saturated sodium bicarbonate aqueous solution, the organic phase was separated, washed with brine and then dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=60:1) to obtain a colorless oily title compound (5.5 g, 56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07910619B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-f575734f517d4f549509e9638ed86b05 |
| Source note | uspto-grants-2011_03 |