248920-11-8

Basic information

• Product Name: 2-bromo-3-methylphenyl acetic acid
• Synonyms: 2-bromo-3-methylphenyl acetic acid
• CAS NO: 248920-11-8
• Molecular Weight: 229.073
• Mol File: 248920-11-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-bromo-3-methylphenyl acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-3-methylphenyl acetic acid(248920-11-8)
• EPA Substance Registry System: 2-bromo-3-methylphenyl acetic acid(248920-11-8)

Safety Data

• Hazardous Substances Data: 248920-11-8(Hazardous Substances Data)

Upstream product

• 248920-09-4 2-(2’-bromo-3’-methylphenyl)acetonitrile 
• 66790-58-7 2-bromo-1-(bromomethyl)-3-methylbenzene 
• 621-36-3 m-methylphenylacetic acid 
• 576-22-7 2-Bromo-m-xylene 

Downstream Products

• 248920-15-2 2-(2-bromo-3-methylphenyl)ethanol 
• 512786-36-6 (2-bromo-3-methyl-phenyl)-acetic acid methyl ester 
• 1372409-15-8 C₁₉H₂₂BrN 
• 1372409-10-3 C₁₉H₂₂BrN 
• 950779-46-1 C₁₅H₁₇BrN₂ 

Relevant articles and documents

Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp3)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process

Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C(sp3)-H bond functionalization triggered by a sequential hydride shift/cyclization process. This reaction consists of stereoselective domino C(sp3)-H bond functionalization: (1) a highly enantio- and diastereoselective C(sp3)-H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereoselective C(sp3)-H bond functionalization by an achiral catalyst (Yb(OTf)3, second [1,5]-hydride shift).

Optimization and scale-up of a Pd-catalyzed aromatic C-N bond formation: A key step in the synthesis of a novel 5-HT1B receptor antagonist

Searching for the best synthetic route for a given target molecule is a complex task and, by the same token, a key deliverable from a process R&D department. In this vein the challenge for our group was to identify a sustainable manufacturing process for a chiral compound, AR-A2, to be developed for the treatment of certain neurological disorders. Besides designing a method for assembling the core (R)-2-aminotetralin nucleus, a key feature in the overall synthesis was to provide a robust procedure for creating a new C-N bond between an aromatic ring and a heterocyclic moiety. The methodology employed a Buchwald-Hartwig coupling, and a highly efficient catalytic process was developed using Pd(OAc)2 as precatalyst, with loadings as low as 0.47 mol % (in laboratory trials one order of magnitude lower) together with (R)-BINAP as ligand. Optimizing the reaction conditions allowed a virtually quantitative conversion of the brominated aromatic substrate after heating to 110-115 °C in toluene for 4 h. Telescoping this step with a succeeding catalytic hydrogenation to effect an N-debenzylation, followed by precipitation of the benzoate salt offered an overall yield for the two consecutive steps of 88% at 125-kg batch size, combined with excellent stereochemical product purity of 98% ee.