(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

Safety Information

HS Code 

2932190090

(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(915095-89-5)Related Product Information

• 2,3-Butanediol
• Empagliflozin (R)-Isomer
• Empagliflozin Impurity 23
• Acetoxy Empagliflozin
• ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate
• N/A
• Butanoic acid, 4-chloro-3-hydroxy-, (3S)-
• (S)-3-(4-benzylphenoxy)tetrahydrofuran
• (R)-3-(p-toluenesulfonyl) oxytetrahydrofuran
• Empagliflozin
• (S)-(+)-3-Hydroxytetrahydrofuran
• 4-(5-broMo-2-chlorobenzyl)phenol
• Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]-
• (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone
• (2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol
• 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide
• (S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran
• (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone