HuagongsheHuagongshe Chemistry Print Report · For research reference only
Boron trifluoride etherate → 2-(5-Bromo-2-methoxybenzyl)-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-methoxyphenyl)methanol | HCID 61406666 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | 2-(5-Bromo-2-methoxybenzyl)-1-benzothiophene | HCID 18450460 | 92% |
Reaction Steps
Then, Et3SiH (10.3 mL, 0.0642 mol) and BF3.Et2O (4.10 mL, 0.0321 mol) were added sequentially to a chloroform (110 mL) solution of (1-benzothien-2-yl)(5-bromo-2-methoxyphenyl)methanol (1.2 g, 0.0321 mol) at −15° C. After the mixture was stirred for 0.5 hours, a saturated sodium bicarbonate aqueous solution was added. The mixture was extracted with chloroform, and the organic phase was washed with brine and then dried with anhydrous magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain a title compound (9.84 g, 92%) as a yellow crystal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08017792B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-b76daecdca7348f18a8a300537ef0d3f |
| Source note | uspto-grants-2011_09 |