(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran

CAS No.：915095-89-5

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(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Basic information

Description Physical Form synthesis

Product Name:	(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran
Synonyms:	EMpagliflozin int3;Empagliflozin-7;915085-89-5;Empagliflozin Bromo Impurity;(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)-benzene;3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-;(3S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydro-furan;(3S)-3-[4-[(5-bromo-2-chlorophenyl)methyl]phenoxy]oxolane 915095-89-5
CAS:	915095-89-5
MF:	C17H16BrClO2
MW:	367.66
EINECS:	1592732-453-0
Product Categories:	Empagliflozin Intermediate
Mol File:	915095-89-5.mol

(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

Safety Information

HS Code

2932190090

MSDS Information

(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.
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

Raw materials

(5-broMo-2-chlorophenyl)(4-hydroxyphenyl)Methanone-->(R)-(-)-3-Hydroxytetrahydrofuran-->5-BROMO-2-CHLORO-BENZOYL CHLORIDE-->(S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone-->(5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone-->4-bromo-2-(bromomethyl)-1-chlorobenzene-->4-(5-broMo-2-chlorobenzyl)phenol-->5-Bromo-2-chlorobenzoic acid-->(S)-(+)-3-Hydroxytetrahydrofuran-->4-Bromoaniline-->Fluorobenzene-->p-Fluorotoluene

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