915133-57-2

Usage

Uses

Used in Pharmaceutical Industry:
2,2-difluoro-2-(3-methoxyphenyl)acetic acid ethyl ester is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structural features, including the difluoromethyl and methoxyphenyl groups, contribute to the development of new drugs with improved pharmacological properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2,2-difluoro-2-(3-methoxyphenyl)acetic acid ethyl ester is utilized as a precursor in the production of agrochemicals. Its reactivity and structural attributes make it suitable for the synthesis of novel agrochemicals with enhanced efficacy and selectivity.
Used as a Building Block in Drug Production:
2,2-difluoro-2-(3-methoxyphenyl)acetic acid ethyl ester is employed as a key building block in the manufacturing process of diverse drugs. Its incorporation into the molecular structure of these drugs allows for the creation of pharmaceuticals with specific therapeutic effects and improved pharmacokinetic profiles.

Upstream product

• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 667-27-6 Ethyl bromodifluoroacetate 
• 100-66-3 methoxybenzene 
• 66107-33-3 3-methoxyphenyl triflate 
• 205865-67-4 α-(trimethylsilyl)difluoroacetic acid ethyl ester 
• 766-85-8 3-methoxy-1-iodobenzene 

Downstream Products

• 1393726-82-3 2,2-difluoro-2-(3-methoxyphenyl)acetamide 
• 1393560-28-5 2,2-difluoro-2-(3-methoxyphenyl)ethylamine 
• 1393726-84-5 5-[2,2-difluoro-2-(3-methoxyphenyl)ethyl]-1,3,5-dioxazinane 
• 1393726-83-4 1,3,5-tris[2,2-difluoro-2-(3-methoxyphenyl)ethyl]-1,3,5-triazinane 
• 454-90-0 3-(trifluoromethyl)anisole 
• 1027513-99-0 2,2-difluoro-2-(3-methoxyphenyl)acetic acid 

Relevant academic research and scientific papers

Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C-H/N-H Coupling

Herein, a direct method for the synthesis of 3-fluoroindoles and 3,3-difluoroindolines from easily accessible 2,2-difluoro-2-phenyl ethan-1-amines is presented. This protocol was performed by Pd-catalyzed direct C-H/N-H coupling and employed picolinamide as a directing group. By controlling the temperature for this transformation, various 3,3-difluoroindolines and 3-fluoroindoles could be isolated with moderate to good yields.

Synthetic method of aromatic ring group or aromatic heterocyclic tetrazole

The synthetic method comprises the following steps: (1) reacting 1.0 eq of ArI or HArI with 1.2 eq of ethyl 2, 2-difluoroacetate in the presence of DMSO as a solvent and 4.0 eq of Cu under the protection of nitrogen at 30 DEG C and 50 DEG C, and purifying to obtain a first intermediate compound; (2) dissolving 1.0 eq of the first intermediate compound in a mixed solvent of THF and water, adding 2.0 eq of LiOH, reacting at room temperature for 2 hours, spin-drying the solvent, adding HCl until the pH value is equal to 3, and filtering to obtain a second intermediate compound; and (3) reacting 1.0 eq of the second intermediate compound with 2.0 eq of diphenyl azide phosphate in the presence of 2.5 eq of triethylamine by taking tert-butyl alcohol as a solvent to generate aromatic ring group or aromatic heterocyclic tetrazole. The invention provides a novel synthetic method of aromatic ring group or aromatic heterocyclic tetrazole, wherein a target compound can be more conveniently obtained, and reagents participating in the reaction are low in toxicity, mild in reaction condition, simple and safe in aftertreatment, good in product quality and suitable for large-scale production.

Palladium-Catalyzed Cross-Coupling of Ethyl Bromodifluoroacetate with Aryl Bromides or Triflates and Cross-Coupling of Ethyl Bromofluoroacetate with Aryl Iodides

A palladium-catalyzed Negishi cross-coupling reaction of ethyl bromodifluoroacetate with aryl bromides or aryl triflates to construct C(sp2)-CF2 bonds is described. The reaction was conducted under mild reaction conditions, and no preparation of organozinc reagents is required. This is the first report encompassing the conversion of aryl triflates into products containing C-CF2 bonds. In addition, the construction of C(sp2)-CHF bonds was achieved under mild conditions via a cross-coupling of aryl iodides with ethyl bromofluoroacetate.

Silver-Catalyzed Decarboxylative Radical Addition/Cyclization of α,α-Difluoroarylacetic Acids with Acrylamides To Synthesize Difluorinated Oxindoles

A facile silver-catalyzed decarboxylative radical addition/cyclization reaction of α,α-difluoroarylacetic acids and acrylamides has been disclosed. The method provides a highly attractive approach to synthesize a series of difluorinated oxindoles that contain various functional groups in moderate to good yields under mild conditions. Moreover, experimental studies reveal that the CF2 group of the α,α-difluoroarylacetic acids plays a vital role in the transformation.

Silver-Mediated C–H Difluoromethylation of Arenes

The first AgI-mediated C–H ethoxycarbonyl difluoromethylation with TMSCF2COOEt (TMS = trimethylsilyl) has been developed. The radical difluoromethylation proceeds smoothly to give the difluoromethylated arenes in moderate to high yie

Silver-Mediated 18F-Labeling of Aryl-CF3 and Aryl-CHF2 with 18F-Fluoride

We report the synthesis of [18F]arylCF3 and [18F]arylCHF2 derivatives from arylCF2Br and arylCHFCl precursors applying a silver-mediated halogen exchange with [18F]fluoride. In the absence of Ag(I)OTf, no reaction takes place at room temperature for both classes of substrates; this result demonstrates the beneficial role of silver(I) as a means to induce 18F-incorporation under very mild conditions.

Copper-catalyzed innate ethoxycarbonyldifluoromethylation of electron-rich arenes

We report the direct introduction of the CF2CO2Et moiety into electron-rich arenes. The copper-catalyzed process uses commercially available and inexpensive BrCF2CO2Et as a fluorinated building block. This radic

Visible Light-Induced Aromatic Difluoroalkylation

Difluoroalkylated aromatics are important structural motifs in pharmaceutical and agrochemical applications. Herein, we report their synthesis by a mild, efficient, and convenient method using visible light photoredox catalysis. A variety of unactivated aromatics were difluoroalkylated with ethyl 2-bromo-2,2-difluoroacetate (BrCF2CO2Et) in the presence of the triscyclometalated Ir complex fac-[Ir(ppy)3] under visible light irradiation at room temperature. It is shown that reaction outcomes containing the CF2CO2Et moiety can be converted to a variety of other CF2-containing aromatics, demonstrating the synthetic utility of the present method.

Cobalt-catalyzed cross-coupling reaction of arylzinc reagents with ethyl bromodifluoroacetate

Transition metal-catalyzed cross-coupling reactions of arylmetal reagents with ethyl bromodifluoroacetate have been explored. After intensive investigations, we have successfully found that a cobalt-catalyzed cross-coupling reaction (catalytic alkoxycarbonyldifluoromethylation) of arylzinc reagents with ethyl bromodifluoroacetate smoothly proceeded to afford the corresponding ethyl aryldifluoroacetates in moderate to good yields.

Catalytic decarboxylative fluorination for the synthesis of Tri- and difluoromethyl arenes

Treatment of readily available α,α-difluoro- and α-fluoroarylacetic acids with Selectfluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [18F]labeling is demonstrated using [ 18F]Selectfluor bis(triflate), a reagent affording [ 18F]tri- and [18F]difluoromethylarenes not within reach with [18F]F2.