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| | (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Chemical Properties |
| Melting point | 49-51°C | | Boiling point | 459.1±45.0 °C(Predicted) | | density | 1.431±0.06 g/cm3 (20 ºC 760 Torr) | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | color | White to Off-White | | InChI | InChI=1S/C17H16BrClO2/c18-14-3-6-17(19)13(10-14)9-12-1-4-15(5-2-12)21-16-7-8-20-11-16/h1-6,10,16H,7-9,11H2/t16-/m0/s1 | | InChIKey | HUNLNKBDQXGMAP-INIZCTEOSA-N | | SMILES | O1CC[C@H](OC2=CC=C(CC3=CC(Br)=CC=C3Cl)C=C2)C1 |
| | (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Usage And Synthesis |
| Description | (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is
used as a reactant to efficiently synthesize SGLT- 2 Epagliflozin
inhibitors. | | Physical Form | Solid | | synthesis | To a mixture of AlCl3 (61.7 g, 0.463 mol) and (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (100 g, 0.231 mol) in toluene (450 mL) was added 1,1,3,3-tetramethyldisiloxane (40.4 g, 0.301 mol) over 1 hour at<20 °C. The mixture was held at 20-23 °C for an additional 1.5 hours and cooled to 0-5 °C. The cooled solution was slowly added to ice-water (400 mL) over 15 min and the layers separated. The organic was treated with 3N NaOH (400 mL) at room temperature for 16-24 hours and the layers were separated. The organic was concentrated to a low volume (~130 mL). After diluted with acetonitrile (450 mL), the solution was again concentrated to a low volume (~130 mL). To the residue was added acetonitrile (400 mL) followed by a slow addition of water (200 mL). The resulting mixture was cooled to 0-3 °C and held for 2 hours. The solids were collected by filtration and dried in oven to give product. (S)-3-(4-(2-chloro-5- bromobenzyl)phenoxy)tetrahydrofuran (2a). 92% as white crystals.
![synthesis of (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran](https://www.chemicalbook.com/NewsImg/2022-08-16/6379623720565357024820368.jpg "synthesis of (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran") | | Uses | (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is used as a reactant in the efficient synthesis of empagliflozin inhibitor of SGLT-2 utilizing AlCl3-promoted silane reduction of β-glycopyranoside. |
| | (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Preparation Products And Raw materials |
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