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Basic Information
CAS No.: 79232-66-9
Name: Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)-
Molecular Structure:
Molecular Structure of 79232-66-9 (Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)-)
Formula: C5H6 Br N O4
Molecular Weight: 224.011
Synonyms: Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(Z)-; (Z)-4-Bromo-3-oxo-2-methoxyiminobutyric acid
PSA: 75.96000
LogP: 0.03740
Synthetic route
79232-65-8

2-Methoxyiminoacetoacetic acid-tert-butyl ester

79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

Conditions
ConditionsYield
With chloro-trimethyl-silane; bromine; triethylamine; trifluoroacetic acid In tetrachloromethane; hexane; dichloromethane; nitrogen; water; acetonitrile70.5%
With bromine In 5,5-dimethyl-1,3-cyclohexadiene; di-isopropyl ether; water42.4%
77361-12-7

(Z)-2-methoxyimino-3-oxo-butyric acid

79232-65-8

2-Methoxyiminoacetoacetic acid-tert-butyl ester

79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

Conditions
ConditionsYield
With hydrogen bromide; bromine In dichloromethane; water; acetic acid; trifluoroacetic acid
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

77361-11-6

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride

Conditions
ConditionsYield
With phosphorus pentachloride In hexane; dichloromethane96%
With phosphorus pentachloride In dichloromethane at -20 - -5℃; Product distribution / selectivity;
With phosphorus pentachloride In dichloromethane
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

N,N-dimethylformiminium chloride chlorosulphate

4-bromo-2(Z)-methoxyimino-3-oxo butyric acid-N,N-dimethyl formiminium chloride chlorosulfate

Conditions
ConditionsYield
In dichloromethane at -25 - 10℃; for 2.5h;
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

1056123-64-8

4-bromo-2-methoxyimino-3-oxo butyric acid chloride

Conditions
ConditionsYield
With phosphorus pentachloride In dichloromethane at -25 - -20℃; for 0.666667h;
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

79-37-8

oxalyl dichloride

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

77361-11-6

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride

B

4-bromo-2-methoxyimino-3-oxobutyrl chloride

4-bromo-2-methoxyimino-3-oxobutyrl chloride

Conditions
ConditionsYield
In dichloromethane
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

10026-13-8, 874483-75-7

phosphorus pentachloride

77361-11-6

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride

Conditions
ConditionsYield
In dichloromethane
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

phosphorus oxy chloride

phosphorus oxy chloride

3004-42-0

2-Mercapto-5-phenyl-1,3,4-oxadiazole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-4-bromo-2-methoxyimino-3-oxo-butyrate

Conditions
ConditionsYield
With pyridine In acetonitrile
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

Benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride

trimethylsilylacetamide

benzhydryl 7-(4-bromo-2-methoxyiminoacetoacetamido)-3-vinyl-3-cephem-4-carboxylate

Conditions
ConditionsYield
With trichlorophosphate In water; ethyl acetate; N,N-dimethyl-formamide
With trichlorophosphate In water; ethyl acetate; N,N-dimethyl-formamide
79232-66-9

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid

C24H28N2O6S2Si

7-[2-(syn)methoxyimino-3-oxo-4-bromobutyrylamino]-3-[(fur-2-ylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester

Conditions
ConditionsYield
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;
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