Literature DB >> 35364809

Resolving Bromonitromethane Sourcing by Synthesis: Preparation at the Decagram Scale.

Madelaine P Thorpe1, Abigail N Smith1, Michael S Crocker1, Jeffrey N Johnston1.   

Abstract

The accessibility of bromonitromethane has declined in recent years, limiting its viability as a reagent for chemical synthesis. The reinvestigation and optimization of a variety of preparations, and the development of safe operating principles, are described. The reproducible protocol described here leverages the effectiveness of hydroxide for nitromethane bromination while respecting its incompatibility with the product it forms. This careful balance was achieved at scales up to 56 g, resulting in a reproducible procedure that provides straightforward, sustainable, and affordable access to this critical reagent.

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Year:  2022        PMID: 35364809      PMCID: PMC9109156          DOI: 10.1021/acs.joc.2c00405

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.198


  6 in total

1.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

2.  Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert-Butyl ((1R)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate.

Authors:  Victoria T Lim; Sergey V Tsukanov; Amanda B Stephens; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2016

3.  Efficient addition reaction of bromonitromethane to aldehydes catalyzed by NaI: a new route to 1-bromo-1-nitroalkan-2-ols under very mild conditions.

Authors:  José M Concellón; Humberto Rodríguez-Solla; Carmen Concellón; Santiago García-Granda; M Rosario Díaz
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

4.  Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid-Base Catalyst with Recycle.

Authors:  Sergey V Tsukanov; Martin D Johnson; Scott A May; Morgan Rosemeyer; Michael A Watkins; Stanley P Kolis; Matthew H Yates; Jeffrey N Johnston
Journal:  Org Process Res Dev       Date:  2016-02-01       Impact factor: 3.317

5.  Chiral proton catalysis: a catalytic enantioselective direct aza-Henry reaction.

Authors:  Benjamin M Nugent; Ryan A Yoder; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

6.  Enantioselective Synthesis of D-α-Amino Amides from Aliphatic Aldehydes.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825

  6 in total

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