(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone Chemical Properties

Boiling point:

439.2±40.0 °C(Predicted)

Density 

1.437

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Low-Melting Solid

color 

Off-White to Pale Yellow

InChI

InChI=1S/C15H12BrClO2/c1-2-19-12-6-3-10(4-7-12)15(18)13-9-11(16)5-8-14(13)17/h3-9H,2H2,1H3

InChIKey

OEURLNJEQCLGPS-UHFFFAOYSA-N

SMILES

C(C1=CC(Br)=CC=C1Cl)(C1=CC=C(OCC)C=C1)=O

CAS DataBase Reference

461432-22-4

(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone Usage And Synthesis

Uses

(5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone is an intermediate used in the improved synthesis of Dapagliflozin, a novel selective sodium-glucose co-transporter type II (SGLT2) inhibitor.

Synthesis

Under the protection of nitrogen, 2.1 g of tert-butyldimethylchlorosilane prepared in step 1) was mixed with 5-bromo-2-chlorobenzoyl chloride in anhydrous dichloromethane and stirred for 30 min at 0 to 10 °C. Subsequently, 1.2 mol of phenethyl ether and 1.1 mol of ferric chloride were sequentially added to the reaction system, and the reaction temperature was maintained at 14.7 °C, and the reaction continued to be stirred for 5 hours. After completion of the reaction, the reaction mixture was quenched by pouring it into ice water, extracted with dichloromethane, the organic phase was washed with water, and 31 g of 5-bromo-2-chloro-4'-ethoxy benzophenone (intermediate of dagliflozin) was obtained after concentration in 91.4% yield and 99.49% purity.

References

[1] Patent: CN107200683, 2017, A. Location in patent: Paragraph 0029; 0035; 0039; 0043; 0047
[2] Patent: CN107417515, 2017, A. Location in patent: Paragraph 0030; 0032; 0034; 0036; 0038; 0040
[3] Patent: CN103739581, 2016, B. Location in patent: Paragraph 0228; 0229
[4] Patent: WO2012/25857, 2012, A1. Location in patent: Page/Page column 20
[5] Patent: CN106316803, 2017, A. Location in patent: Paragraph 0014

(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone(461432-22-4)Related Product Information

• (5-broMo-2-chloro-phenyl)-(4-ethoxy-phenyl)-Methanone
• Dapagliflozin
• Dapagliflozin iMpurity
• BMS-639432
• (2S,3R,4R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-5-((S)-1,2-dihydroxyethyl)tetrahydrofuran-3,4-diol
• (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxyMethyl)tetrahydro-2H-pyran-3,4,5-triol
• Dapagliflozin Open Ring
• (1-Bromoethyl)benzene
• 2-Bromotoluene
• 4,4'-DDT
• Rivaroxaban
• 1-Chloro-2-(4-ethoxybenzyl)-4-iodobenzene
• 5-bromo-2-chloro-4’-ethoxydiphenylmethane
• 4-BROMO-1-CHLORO-2-ETHYLBENZENE
• 3-BROMO-4''-METHOXYBENZOPHENONE
• 3-BROMO-4'-ETHOXYBENZOPHENONE
• (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone
• 2-CHLORO-4'-ETHOXYBENZOPHENONE