| Identification | More | [Name]
ETHYL5-ACETOXY-6-BROMO-2-(BROMOMETHYL)-1-METHYLINDOLE-3-. | [CAS]
110543-98-1 | [Synonyms]
ETHYL5-ACETOXY-6-BROMO-2-(BROMOMETHYL)-1-METHYLINDOLE-3-.
Ethyl 5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-carboxylate | [Molecular Formula]
C15H15Br2NO4 | [MDL Number]
MFCD00407019 | [Molecular Weight]
433.09 | [MOL File]
110543-98-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
168-171 °C(Solv: carbon tetrachloride (56-23-5)) | [Boiling point ]
529.8±50.0 °C(Predicted) | [density ]
1.67±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [Appearance]
Brown to gray Solid | [InChI]
InChI=1S/C15H15Br2NO4/c1-4-21-15(20)14-9-5-13(22-8(2)19)10(17)6-11(9)18(3)12(14)7-16/h5-6H,4,7H2,1-3H3 | [InChIKey]
MESMQGKAVXOGHJ-UHFFFAOYSA-N | [SMILES]
N1(C)C2=C(C=C(OC(C)=O)C(Br)=C2)C(C(OCC)=O)=C1CBr | [CAS DataBase Reference]
110543-98-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of ethyl 1-methyl-2-(bromomethyl)-5-acetoxy-6-bromoindole-3-carboxylate from ethyl 5-acetoxy-1,2-dimethylindole-3-carboxylate: 137.6 g (0.45 mol) of ethyl 5-acetoxy-1,2-dimethylindole-3-carboxylate was dissolved in 1000 mL of chloroform with stirring until completely dissolved. A catalytic amount of benzoyl peroxide was added and heated to reflux. 64.0 mL (200 g, 1.25 mol) of liquid bromine was added slowly dropwise and the reaction was continued at reflux for 3 hours after completion of the dropwise addition. Upon completion of the reaction, the reaction mixture was cooled to room temperature and a solid was precipitated. The solid was washed with a small amount of methanol and dried to give 184.0 g of ethyl 1-methyl-2-(bromomethyl)-5-acetoxy-6-bromoindole-3-carboxylate in 85.0% yield. | [References]
[1] Pharmaceutical Chemistry Journal, 1993, vol. 27, # 1, p. 75 - 76
[2] Khimiko-Farmatsevticheskii Zhurnal, 1993, vol. 27, # 1, p. 70 - 71
[3] Patent: CN106083691, 2016, A. Location in patent: Paragraph 0025; 0055; 0056
[4] Patent: US5198552, 1993, A
[5] Patent: EP1731506, 2006, A1. Location in patent: Page/Page column 12; 16 |
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