203314-28-7

2-(2,5-Dibromophenyl)acetic Acid is used as a reactant in the synthesis of MK-8742, a HCV NS5a inhibitor.

In a 500 mL four-necked reaction flask, 82 g of 2-(2,5-dibromophenyl)acetonitrile was added to 400 mL of aqueous 2 N sodium hydroxide, and the mixture was heated to 100 °C and refluxed. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with 36% hydrochloric acid by slow dropwise addition to 8. The aqueous layer was separated by extraction with ethyl acetate. Subsequently, the pH of the aqueous layer was adjusted to 1-2 with 36% hydrochloric acid, at which point a solid precipitated. The off-white solid 2-(2,5-dibromophenyl)acetic acid was collected by filtration and dried to give 73 g in 83% yield.

[1] Patent: CN107759459, 2018, A. Location in patent: Paragraph 0007; 0008; 0017; 0018
[2] Synlett, 2011, # 17, p. 2525 - 2528
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3563 - 3580