1-BROMO-2-NAPHTHOIC ACID

Chemical Properties

Solid

Uses

Reactant involved in synthesis of:

• Binaphthyl-based amino acids and amino alcohols via domino coupling reactions and lactam ring opening of intermediates
• Benzimidazoles and benzimidazolequinone derivatives via cyclocondensation
• Axially chiral biaryls via Suzuki-Miyaura reactions
• Aryl ring-fused benzimidazolequinones via radical cyclization
• Probes for human cytochrome P450 enzymes
• Phananthridinone derivatives via domino coupling reactions

Uses

1-Bromo-2-naphthoic acid is a reactant involved in synthesis of:• ;Binaphthyl-based amino acids and amino alcohols via domino coupling reactions and lactam ring opening of intermediates• ;Benzimidazoles and benzimidazolequinone derivatives via cyclocondensation• ;Axially chiral biaryls via Suzuki-Miyaura reactions• ;Aryl ring-fused benzimidazolequinones via radical cyclization• ;Probes for human cytochrome P450 enzymes• ;Phananthridinone derivatives via domino coupling reactions.

Synthesis

76635-70-6

20717-79-7

4) 1.59 g of 2-hydroxymethyl-1-bromonaphthalene and 22 mL of acetone were added to a 250 mL round bottom flask and heated to reflux. 3.67 g of potassium permanganate was dissolved in 8.1 mL of water and 55 mL of acetone, heated and slowly added to the round-bottomed flask, and the reaction mixture was maintained at reflux for 30 min, then continued at reflux for 5 hr. The solution gradually turned brown during the reaction and the heating was stopped when the reaction was completed. The reaction mixture was filtered to remove the resulting MnO2 solid precipitate and the precipitate was washed with ether. Concentration of the filtrate gave 1.32 g of the target product 1-bromo-2-naphthoic acid in 78.6% yield.

References

[1] Patent: CN105541605, 2016, A. Location in patent: Paragraph 0017; 0026; 0035; 0044; 0071; 0080
[2] Journal of Organic Chemistry, 1983, vol. 48, # 21, p. 3869 - 3876