| Identification | Back Directory | [Name]
Furan, 3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-, (3S)- | [CAS]
915095-89-5 | [Synonyms]
915085-89-5
Empagliflozin-7
EMpagliflozin int3
EMpagliflozin InterMediate
Empagliflozin Intermediate2
Empa (S)-THF bromo compound
Empagliflozin Bromo Impurity
5-Bromo Empagliflozin Impurity
(S)-3-(4-(5-broMo-2-chlorobenzyl)phenoxy)tetrahydrofuran
3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-
(3S)-3-[4-[(5-bromo-2-chlorophenyl)methyl]phenoxy]oxolane
(3S)-3-[4-(5-Bromo-2-chlorobenzyI)phenoxy]tetrahydrofuran
(3S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydro-furan
(3S)-3-[4-(5-bromo-2-chloro benzyl) phenoxy] tertahydrofuran
3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-furan
(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro...
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)-benzene
(3S)-3-(4-(5-bromo-2-chlorobenzyl) methyl]phenoxy]tetrahydro-furan
(35)-3-[4-[(5-Bromo-2-chlorophenyl)methyllphenoxyltetrahydro-furan
(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan
(3S)-3-[4-[(5-Bromo-2- chlorophenyl)methy1]phenoxy]tetrahydro-furan
(3S)-3-[4-[(5-bromo-2-chlorophenyl)methyl]phenoxy]oxolane 915095-89-5
Furan, 3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-, (3S)-
3S-{4-[Benzyloxy-(5-bromo-2-chloro-phenyl)-methyl]
-phenoxy}-tetrahydro-furan
(3S)-3-[4-[(5-BROMO-2-CHLOROPHENYL)METHYL]PHENOXY]TETRAHYDRO-FURAN CAS NO 915095-89-5
Furan, 3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-, (3S)- ISO 9001：2015 REACH
Empagliflozin Intermediate/ (3S)-3-[4-[(5-Bromo-2-Chlorophenyl)Methyl]Phenoxy]Tetrahydrofuran
Empagliflozin impurity 10/Empagliflozin 5-Bromo Impurity/(S)-3-[4-(5-Bromo-2-chlorobenzyl)phenoxy]tetrahydrofuran | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C17H16BrClO2 | [MDL Number]
MFCD27920793 | [MOL File]
915095-89-5.mol | [Molecular Weight]
367.665 |
| Questions And Answer | Back Directory | [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") |
| Chemical Properties | Back Directory | [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 | [Optical Rotation]
Consistent with structure | [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 |
| Hazard Information | Back Directory | [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. | [Application]
(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. | [References]
[1] Organic Letters, 2014, vol. 16, # 16, p. 4090 - 4093
[2] Patent: CN106905305, 2017, A. Location in patent: Paragraph 0056; 00057; 0058; 0059
[3] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 24-25
[4] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 25
[5] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 25 |
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