ChemicalBook CAS DataBase List 5-Bromo-2-hydroxy-4,6-dimethyl-nicotinonitrile

5-Bromo-2-hydroxy-4,6-dimethyl-nicotinonitrile synthesis

4synthesis methods

Product Name:5-Bromo-2-hydroxy-4,6-dimethyl-nicotinonitrile
CAS Number:814262-90-3
Molecular formula:C14H12O4
Molecular Weight:244.24

Benzoic acid, 5-[[(4-methylphenyl)sulfonyl]oxy]-2-(phenylmethoxy)-, methyl ester

1285516-29-1
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5-Bromo-2-hydroxy-4,6-dimethyl-nicotinonitrile

814262-90-3
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Yield:-

Reaction Conditions:

Stage #1: methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoatewith water;potassium hydroxide in ethanol;Reflux;
Stage #2: with hydrogenchloride in water;ethyl acetate;Product distribution / selectivity;

Steps:

38.C

Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 75; 22.0 g, 53.3 mmol) was boiled with potassium hydroxide (20.95 g, 373 mmol) in a mixture of ethanol (320 ml) and water (80 ml) overnight. After the ethanol had been evaporated, the aqueous solution was washed with ethyl acetate (500 mi), and then acidified with concentrated HCI. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over sodium sulfate, and evaporated in vacuo to yield the title compound as a yellow oil. 14 g.MS (electrospray): m/z [MH+ 23]⁺ = 267

References:

WO2011/38572,2011,A1 Location in patent:Page/Page column 60

2150-46-1 Synthesis