| Identification | Back Directory | [Name]
2,5-Dibromophenylacetic acid | [CAS]
203314-28-7 | [Synonyms]
Dibromophenylacetic acid
5-Dibromophenylacetic acid
2,5-Dibromophenylacetic acid
2,5-Dibromobenzeneacetic acid
Benzeneacetic acid, 2,5-dibromo-
2-(2,5-DibroMophenyl)acetic acid | [Molecular Formula]
C8H6Br2O2 | [MDL Number]
MFCD02664691 | [MOL File]
203314-28-7.mol | [Molecular Weight]
293.94 |
| Chemical Properties | Back Directory | [Boiling point ]
376.4±27.0 °C(Predicted) | [density ]
1.969±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
claggy powder | [pka]
3.87±0.10(Predicted) | [color ]
Cream to faint tan | [InChI]
InChI=1S/C8H6Br2O2/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3H,4H2,(H,11,12) | [InChIKey]
NKZKFWYEXDBOTP-UHFFFAOYSA-N | [SMILES]
C1(CC(O)=O)=CC(Br)=CC=C1Br |
| Hazard Information | Back Directory | [Uses]
2-(2,5-Dibromophenyl)acetic Acid is used as a reactant in the synthesis of MK-8742, a HCV NS5a inhibitor. | [Synthesis]
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. | [References]
[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 |
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