420-94-0

Usage

Uses

Used in Pharmaceutical Industry:
2-bromo-2,2-difluoroethan-1-ol is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its reactivity allows for the creation of a wide range of drug molecules, contributing to the development of new medications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-bromo-2,2-difluoroethan-1-ol serves as a building block for the production of various agrochemicals. Its ability to participate in multiple chemical reactions makes it a valuable component in the synthesis of pesticides and other agricultural chemicals.
Safety Precautions:
Due to its toxic nature and potential to cause irritation to the skin, eyes, and respiratory system, proper handling and safety precautions should be taken when working with 2-bromo-2,2-difluoroethan-1-ol. This includes the use of personal protective equipment and ensuring proper ventilation to minimize exposure risks.

Upstream product

• 667-27-6 Ethyl bromodifluoroacetate 

Downstream Products

• 1341215-25-5 2,2-difluoro-2-(3-fluorophenyl)ethanol 
• 1245625-32-4 sodium 1,1-difluoro-2-hydroxyethanesulfinate 

Relevant academic research and scientific papers

A visible-light-mediated radical smiles rearrangement and its application to the synthesis of a difluoro-substituted spirocyclic ORL-1 antagonist

A visible-light-mediated radical Smiles rearrangement has been developed to address the challenging synthesis of the gem-difluoro group present in an opioid receptor-like 1 (ORL-1) antagonist that is currently in development for the treatment of depressio

Preparative Scale Demonstration and Mechanistic Investigation of a Visible Light-Mediated Radical Smiles Rearrangement

A visible light-mediated Smiles rearrangement providing the difluoroethanol motif has been shown to reliably operate on preparative scale up to 100 g of starting material. Mechanistic investigation has revealed the reaction proceeds predominantly via a radical chain process that in some instances can be initiated via visible light or thermal activation in the absence of a photocatalyst. The reaction was demonstrated in continuous flow, with visible light and thermal initiation using a thiophene substrate relevant to pharmaceutical development.

Atom-transfer radical addition of fluoroalkyl bromides to alkenes: Via a photoredox/copper catalytic system

A method for the addition of fluorinated alkyl bromides to alkenes is described. The reaction proceeds under visible light irradiation in the presence of two catalysts: Ir(ppy)3 and N-heterocyclic carbene ligated copper bromide (IMesCuBr). The role of the

Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from: gem -difluorochloro ethanes

Herein, we describe a new transition metal-free Claisen rearrangement for the synthesis of α-substituted 2,4-dienamides. The one-pot, stereoselective three-component cascade reaction between a series of propargyl alcohols, amines, and gem-difluorochloro ethane derivatives afforded various polysubstituted 2,4-dienamides in good yields. This synthetic method for 1,1-captodative dienes, α-substituted 2,4-dienamides, can be utilized for preparing pharmaceutical analogues containing an indolin-2-one or lactone moiety.

Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes

A nickel-catalyzed cross-coupling between (hetero)arylborons and unactivated 1-bromo-1,1-difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine-based ligand, 4,4′-ditBu-bpy, and a monodentate pyridine-based ligand, DMAP) offers a highly efficient nickel-based catalytic system to prepare difluoroalkylated arenes which have important applications in medicinal chemistry. Ligand combo: The title reaction requires the use of a combined (2+1) ligand system, that is, a combination of a bi- and monodentate ligand (4,4′-ditBu-bpy + DMAP). This system allows employment of a wide range of unactivated 1-bromo-1,1-difluoroalkanes as coupling partners, thus providing a highly efficient method for applications in drug discovery and development. bpy=bipyridine, DMAP=4-(N,N-dimethylamino)pyridine.

Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β-Difluoro-α-(trimethylsilyl)alcohols

A methodology allowing the preparation of aldols featuring a fluorinated stereogenic center is reported. The corresponding fluoroenolates are formed in situ from stable β,β-difluoro-α-(trimethylsilyl)alcohols, through a base-mediated process involving a Brook rearrangement followed by a fluoride elimination, and are directly added to aromatic aldehydes. Two different sets of conditions were disclosed. The first one involves the stoichiometric addition of potassium tert-butoxide (t-BuOK) while the second is based on the use of a catalytic amount of an ammonium phenoxide. The latter opens the way for a catalytic and asymmetric version of this Brook/elimination/aldol reaction (BEAR) sequence.

Processes for Production of 2-Bromo-2,2-Difluoroethanol and 2-(Alkylcarbonyloxy)-1,1-Difluoroethanesulfonic Acid Salt

Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.