ETHYL5-ACETOXY-6-BROMO-2-(BROMOMETHYL)-1-METHYLINDOLE-3-. Chemical Properties

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. 

under inert gas (nitrogen or Argon) at 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)

Safety Information

HS Code 

2933998090

ETHYL5-ACETOXY-6-BROMO-2-(BROMOMETHYL)-1-METHYLINDOLE-3-. Usage And Synthesis

Uses

Ethyl 5-acetoxy-6-bromo-2-bromomethyl-1-methylindole-3-carboxylate can be used as an intermediate for Arbidol.

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

ETHYL5-ACETOXY-6-BROMO-2-(BROMOMETHYL)-1-METHYLINDOLE-3-.(110543-98-1)Related Product Information

• 1-Methylindole
• 1-Methyl-1H-indole-3-carboxylic acid