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203314-28-7

203314-28-7 Structure

203314-28-7 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H332-H315-H319-H335
[Precautionary statements ]

P260-P280-P312
[REACH Registrations]

Inactive
[HS Code ]

2916399090
Hazard InformationBack Directory
[Uses]

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

2,5-DIBROMOBENZENE ACETONITRILE

74533-21-4

2,5-Dibromophenylacetic acid

203314-28-7

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
Spectrum DetailBack Directory
[Spectrum Detail]

2,5-Dibromophenylacetic acid(203314-28-7)1HNMR
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