| Identification | Back Directory | [Name]
(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone | [CAS]
461432-22-4 | [Synonyms]
Dapagliflozin-15
Dapagliflozin iMpurity A
Dapagliflozin Impurity 18
Dapagliflozin Intermediate I
Dapagliflozin Bromomethanone
5-broMo-2-chloro-4'-ethoxybenzophenone
(5-broMo-2-chlorophenyl)(4-ethoxyphenyl)-
(5-BroMo-2-chlorophenyl)(4-ethoxypheny)Methanone
(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone
Methanone, (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)- | [EINECS(EC#)]
630-623-9 | [Molecular Formula]
C15H12BrClO2 | [MDL Number]
MFCD11044417 | [MOL File]
461432-22-4.mol | [Molecular Weight]
339.61 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
|
|