2,4-DIFLUORO-3-METHOXYBENZOYL CHLORIDE synthesis
- Product Name:2,4-DIFLUORO-3-METHOXYBENZOYL CHLORIDE
- CAS Number:221221-11-0
- Molecular formula:C8H5ClF2O2
- Molecular Weight:206.57
178974-97-5
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221221-11-0
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Yield:221221-11-0 100%
Reaction Conditions:
with thionyl chloride in dichloromethane;N,N-dimethyl-formamide at 20;Inert atmosphere;
Steps:
2,4-Difluoro-3-methoxybenzoyl chloride (16)
General procedure: Under inert atmosphere, a mixture of carboxylic acid 6-12 (Scheme 1) (1 equiv), thionyl chloride (1.5 equiv) and DMF (3-5 drops) in dichloromethane was stirred at rt until the complete consumption of the carboxylic acid (1H NMR control). The pale yellow solution was concentrated in vacuo to give the crude acid chloride 13-19 (Scheme 1) as a yellow pale solid in quantitative yield and used without further purification in the condensation reaction with phenothiazine to provide compounds 20-26. 1H NMR (CDCl3, 400MHz) δ (ppm) 4.04 (s, 3H, OCH3), 7.04 (td, J= 9.4, 2.0 Hz, 1H, ArH), 7.83 (sym m,1H, ArH). 19F NMR (CDCl3,376 MHz) δ (ppm) -122.54 (dd, J = 18.4, 7.4 Hz, 1F, ArF),-114.80 (dddd, J = 18.4, 9.6, 5.4 Hz,1F, ArF).
References:
Abuhaie, Cristina-Maria;B?cu, Elena;Rigo, Beno?t;Gautret, Philippe;Belei, Dalila;Farce, Amaury;Dubois, Jo?lle;Ghinet, Alina [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 1,p. 147 - 152] Location in patent:supporting information
178974-97-5
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79-37-8
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221221-11-0
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$60.00/1g
372-18-9
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221221-11-0
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162101-25-9
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221221-11-0
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28177-48-2
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221221-11-0
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$60.00/1g