3196-15-4

Usage

Uses

Used in Chemical Synthesis:
2-Bromobutyric acid methyl ester is used as a reagent for the synthesis of various organic compounds through Reformatsky reactions. It is particularly useful in the production of racemic indene ester via Reformatsky reaction with 5-methoxy-1-indanone and (E)-2-methoxymethylene-butyric acid methyl ester via Reformatsky reaction with α,α-dichloromethyl methyl ether in the presence of zinc dust.
Additionally, it is used in the synthesis of (E)-2-methoxymethylene-butyryl chloride, which is another important intermediate in organic chemistry.

InChI:InChI=1/C5H9BrO2/c1-3-4(6)5(7)8-2/h4H,3H2,1-2H3/t4-/m1/s1

Upstream product

• 17642-18-1 (E)-α-bromocrotonate de methyle 
• 3196-15-4 Methyl 2-bromobutyrate 
• 67-56-1 methanol 
• 22118-12-3 2-bromobutanoyl chloride 
• 107-92-6 butyric acid 
• 141-75-3 butyryl chloride 
• 186581-53-3 diazomethane 
• 80-58-0 2-Bromobutyric acid 
• 2681-94-9 (2R)-2-bromobutanoic acid 

Downstream Products

• 68039-27-0 methyl 2-ethyl-3-oxohexanoate 
• 90794-35-7 2-(2-iodo-phenoxy)-butyric acid 
• 90794-36-8 2-(4-iodo-phenoxy)-butyric acid 
• 90888-05-4 2-(3-Iod-phenoxy)-buttersaeure 
• 554-24-5 2-(2,4,6-triiodo-phenoxy)-butyric acid 
• 91349-85-8 2-(3,5-diiodo-4-methoxy-phenoxy)-butyric acid 
• 90917-53-6 2-(3,5-diiodo-phenoxy)-butyric acid 
• 90917-51-4 2-(2,5-diiodo-phenoxy)-butyric acid 
• 90917-52-5 2-(3,4-diiodo-phenoxy)-butyric acid 
• 90842-74-3 2-(3,4,5-triiodo-phenoxy)-butyric acid 
• 91349-84-7 2-(3,5-diiodo-2-methoxy-phenoxy)-butyric acid 
• 90800-03-6 2-(3,6-dichloro-2,4-diiodo-phenoxy)-butyric acid 
• 13794-14-4 2-phenoxybutyric acid 
• 62916-14-7 2-[2-Cyano-5-(2,6-dichloro-4-trifluoromethyl-phenoxy)-phenoxy]-butyric acid methyl ester 

Relevant academic research and scientific papers

GC separation of enantiomers of alkyl esters of 2-bromo substituted carboxylic acids enantiomers on 6-tbdms-2,3-di-alkyl- β- And γ-cyclodextrin stationary phases

The gas chromatographic separation of enantiomers of 2-Br carboxylic acid derivatives was studied on four different 6-TBDMS-2,3-di-O-alkyl- β- and -γ-CD stationary phases. The differences in thermodynamic data {ΔH and -ΔS} for the 15 structurally related

Cobalt-bisoxazoline-catalyzed asymmetric kumada cross-coupling of racemic α-bromo esters with aryl grignard reagents

The first cobalt-catalyzed asymmetric Kumada cross-coupling with high enantioselectivity has been developed. The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt-bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared in excellent enantioselectivity and yield (up to 97% ee and 96% yield). The arylated products were transformed into α-arylcarboxylic acids and primary alcohols without erosion of ee. The new enantioenriched α-arylpropionic esters synthesized herein are potentially useful in the development of nonsteroidal anti-inflammatory drugs. This method was conducted on gram-scale and applied to the synthesis of highly enantioenriched (S)-fenoprofen and (S)-ar-turmerone.

Enoate reductase-mediated preparation of methyl (S)-2-bromobutanoate, a useful key intermediate for the synthesis of chiral active pharmaceutical ingredients

Enoate reductases belonging to the Old Yellow Enzyme (OYE) family were employed to develop a biocatalysed approach to methyl (S)-2-bromobutanoate, a key intermediate for the introduction of a particular stereogenic unit into the molecular skeleton of a certain class of chiral drugs. Methyl (Z)-2-bromocrotonate afforded, respectively, (S)-2-bromobutanoic acid (ee = 97%) and methyl (S)-2-bromobutanoate (ee = 97%) by baker's yeast fermentation and by OYE1-3 biotransformations. The bioreductions of other methyl 2-haloalkenoates were also considered. It was observed that the (Z)- and (E)-diastereoisomers of α-bromo unsaturated esters afforded the same enantiomer of the corresponding reduced product.

Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering

In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for -bromoesters.

Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals

Bromination of the acetals 4 derived from aryl alkyl ketones, ArCOR, and (2R,3R)-tartaric acid results in bromoacetals 5 with 78-90% de. Hydrolysis of those compounds with Ar = 4-methoxyphenyl or 3-bromo-4-methoxyphenyl results, after recrystallisation, in α-bromoketones 8 with 66-98% ee which are shown to undergo the Baeyer-Villiger oxidation to α-bromoesters 9 with minimal racemisation, α-Bromoketone 8d is shown to undergo carbonyl reduction to threo-bromohydrin 15 with retention of stereochemistry.