ChemicalBook CAS DataBase List Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-

Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)- synthesis

6synthesis methods

Product Name:Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-
CAS Number:1061314-04-2
Molecular formula:C9H6BrClO4
Molecular Weight:293.5

2-Bromo-5-chloro-4-methyl-benzoic acid methyl ester

1061314-02-0
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Benzoic acid, 5-broMo-2-chloro-4-(Methoxycarbonyl)-

1061314-04-2
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Yield:1061314-04-2 73%

Reaction Conditions:

Stage #1: 2-bromo-5-chloro-4-methyl-benzoic acid methyl esterwith 18-crown-6 ether in water;tert-butyl alcohol at 55;Heating / reflux;
Stage #2: with hydrogenchloride in water at 0 - 5; pH=1;

Steps:

4 Preparation of 5-bromo-2-chloro-4-(methoxycarbonyl)benzoic acid (Intermediate K4)

A mixture of methyl 2-bromo-5-chloro-4-methylbenzoate (39.53 g, 0.15 mol), 18-Crown-6 (3.95 g), tert-butyl alcohol (350 mL), and water (750 mL) was combined together with mechanical stirring. The reaction mixture was heated to reflux and monitored by TLC. After refluxing overnight, the reaction was cooled to 55° C. and filtered. The filter cake was washed with hot water (2*100 mL, 50° C.). The filtrate was neutralized with 18% hydrochloric acid to pH 1 and stored in refrigerator (0~5° C.) for 3 h. It was filtered, washed with ice water (2*50 mL) and petroleum ether (2*50 mL). The filter cake was dried under vacuum to give the title compound as a white crystalline. Yield: 32.1 g (73%). ¹H NMR (DMSO-d₆, 300 MHz): δ 8.10 (s, 1H), 7.89 (s, 1H), 3.86 (s, 3H).

References:

US2007/275907,2007,A1 Location in patent:Page/Page column 20

2458-12-0 Synthesis