1-(5-Bromo-2-methoxy-phenyl)adamantane Chemical Properties

Melting point:

139-141°C

Boiling point:

402.5±38.0 °C(Predicted)

Density 

1.346±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

color 

White

InChI

InChI=1S/C17H21BrO/c1-19-16-3-2-14(18)7-15(16)17-8-11-4-12(9-17)6-13(5-11)10-17/h2-3,7,11-13H,4-6,8-10H2,1H3

InChIKey

QQAMHHZQONQBFZ-UHFFFAOYSA-N

SMILES

C12(C3=CC(Br)=CC=C3OC)CC3CC(CC(C3)C1)C2

CAS DataBase Reference

104224-63-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2909309090

1-(5-Bromo-2-methoxy-phenyl)adamantane Usage And Synthesis

Description

1-(5-Bromo-2-methoxy-phenyl)adamantane is an organic synthesis reagent for the preparation of the adapalene intermediate 6-bromo-2-naphthalenecarboxylate.

Chemical Properties

1-(5-Bromo-2-methoxy-phenyl)adamantane Appearance is white Solid or white to light yellow powder to crystalline, melting point 144℃.

Uses

Adapalene (A225000) impurity.

Synthesis

To a stirred mixture of anhydrous N,N-dimethylformamide (5 ml) containing 2-(1-adamantyl)-4-bromophenol (0.5 g; 1.62 mmol) and anhydrous potassium carbonate (0.335 g; 2.42 mmol), iodomethane (1 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was diluted to 100 ml with distilled water and extracted with ethyl acetate (100 ml). The organic layers were combined, dried with anhydrous magnesium sulfate and filtered to remove the desiccant. The filtrate was filtered through silica gel column to remove impurities. Finally, the filtrate was concentrated to dryness under reduced pressure to give 1-(5-bromo-2-methoxyphenyl)adamantane (0.49 g, 94% yield) as a light yellow-green solid.1H-NMR (CDCl3) δ: 7.27-7.22 (m, 2H); 6.31 (d, 1H, J = 6.5 Hz); 3.78 (s, 3H); 2.04 (s, 10H). 1.74 (br, 5H).

References

[1] Patent: WO2010/43000, 2010, A1. Location in patent: Page/Page column 80
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 14, p. 4863 - 4875
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 26, p. 4993 - 5006
[5] Patent: US4717720, 1988, A

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