79232-66-9

Usage

Uses

Used in Agrochemical Industry:
Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)is used as an intermediate in the synthesis of herbicides, specifically as a derivative of cyhalofop. Its application in this industry helps in the development of effective weed control agents, contributing to improved agricultural productivity and crop protection.
Used in Pharmaceutical Industry:
As an intermediate for the synthesis of pharmaceuticals, Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)plays a crucial role in the development of various medicinal compounds. Its unique chemical structure allows it to be a building block for creating new drugs with potential therapeutic applications.
Used in Organic Synthesis:
Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)is also utilized in organic synthesis for the preparation of other organic compounds. Its versatile structure makes it a valuable component in the synthesis of various chemical entities, contributing to the advancement of chemical research and the development of new materials and products.

Synthetic route

2-Methoxyiminoacetoacetic acid-tert-butyl ester (79232-65-8) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9)

Conditions	Yield
With chloro-trimethyl-silane; bromine; triethylamine; trifluoroacetic acid In tetrachloromethane; hexane; dichloromethane; nitrogen; water; acetonitrile	70.5%
With bromine In 5,5-dimethyl-1,3-cyclohexadiene; di-isopropyl ether; water	42.4%

(Z)-2-methoxyimino-3-oxo-butyric acid (77361-12-7) + 2-Methoxyiminoacetoacetic acid-tert-butyl ester (79232-65-8) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9)

Conditions	Yield
With hydrogen bromide; bromine In dichloromethane; water; acetic acid; trifluoroacetic acid

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride (77361-11-6)

Conditions	Yield
With phosphorus pentachloride In hexane; dichloromethane	96%
With phosphorus pentachloride In dichloromethane at -20 - -5℃; Product distribution / selectivity;
With phosphorus pentachloride In dichloromethane

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + N,N-dimethylformiminium chloride chlorosulphate → 4-bromo-2(Z)-methoxyimino-3-oxo butyric acid-N,N-dimethyl formiminium chloride chlorosulfate

Conditions	Yield
In dichloromethane at -25 - 10℃; for 2.5h;

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) → 4-bromo-2-methoxyimino-3-oxo butyric acid chloride (1056123-64-8)

Conditions	Yield
With phosphorus pentachloride In dichloromethane at -25 - -20℃; for 0.666667h;

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + oxalyl dichloride (79-37-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride (77361-11-6) + 4-bromo-2-methoxyimino-3-oxobutyrl chloride

Conditions	Yield
In dichloromethane

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + phosphorus pentachloride (10026-13-8, 874483-75-7) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride (77361-11-6)

Conditions	Yield
In dichloromethane

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + phosphorus oxy chloride + 2-Mercapto-5-phenyl-1,3,4-oxadiazole (3004-42-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-4-bromo-2-methoxyimino-3-oxo-butyrate

Conditions	Yield
With pyridine In acetonitrile

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + Benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride + trimethylsilylacetamide → benzhydryl 7-(4-bromo-2-methoxyiminoacetoacetamido)-3-vinyl-3-cephem-4-carboxylate

Conditions	Yield
With trichlorophosphate In water; ethyl acetate; N,N-dimethyl-formamide
With trichlorophosphate In water; ethyl acetate; N,N-dimethyl-formamide

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + C24H28N2O6S2Si → 7-[2-(syn)methoxyimino-3-oxo-4-bromobutyrylamino]-3-[(fur-2-ylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester

Conditions	Yield
Stage #1: (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid With phosphorus pentachloride In dichloromethane at -30℃; for 0.5h; Stage #2: C24H28N2O6S2Si In dichloromethane at -30℃; for 0.25 - 0.333333h;

Upstream product

• 79232-65-8 2-Methoxyiminoacetoacetic acid-tert-butyl ester 
• 77361-12-7 (Z)-2-methoxyimino-3-oxo-butyric acid 

Downstream Products

• 1056123-64-8 4-bromo-2-methoxyimino-3-oxo butyric acid chloride 
• 77361-11-6 (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride 

Relevant academic research and scientific papers

Process for producing 4-halogeno-2-alkoxyimino-3-oxo fatty acid

4-Halogeno-2-alkoxyimino-3-oxo fatty acid can be produced by one-pot and one-step by reacting a halogenating agent with a 2-alkoxyimino-3-oxo fatty acid ester in an ether solvent or a mixed solvent of an ether solvent and an inert organic solvent such as carbon tetrachloride, benzene, toluene, etc.

Method for production of t-butyl 3-oxobutyrates and their use

Disclosed are an advantageous method of industrial production of tert-butyl 3-oxobutylate, which is a useful intermediate for synthesis, characterized by reacting tert-butyl alcohol with diketene in the presence of 4-(tertiary amino) pyridine, and an industrially advantageous method of producing cephalosporin compounds or pharmaceutically acceptable salts thereof, using tert-butyl 3-oxobutylate as an intermediate.

4-halogeno-2-oxyimino-3-oxobutyric acids and derivatives

A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)-hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.

Acyl derivatives

There are presented compounds of the formula STR1 wherein R1 is one of the 3-substituents usable in cephalosporin chemistry, R2 is hydrogen, lower alkyl or COOR3 -lower alkyl, wherein R3 is hydrogen, a cation of a base or a readily hydrolyzable ester group, and X is sulphur, oxygen or one of the groups --SO-- and --SO2 --, and the readily hydrolyzable esters, readily hydrolyzable ethers and salts of these compounds and hydrates of the compounds of formula I or of their esters, ethers and salts, also presented are methods for the manufacture of these compounds as well as compounds used in their manufacture.