[ CAS No. 50551-61-6 ]

Name: 50551-61-6|6-Methoxybenzofuran-2-carboxylic acid|98%
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COA NMR CNMR HPLC LC-MS

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CAS No. :	50551-61-6	MDL No. :	MFCD06254721
Formula :	C₁₀H₈O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQELKSYGXWBQJA-UHFFFAOYSA-N
M.W :	192.17	Pubchem ID :	918863
Synonyms :

Safety of [ 50551-61-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 50551-61-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 50551-61-6 ]
Downstream synthetic route of [ 50551-61-6 ]

[ 50551-61-6 ] Synthesis Path-Upstream 1~3

1
[ 50551-61-6 ]
[ 50551-63-8 ]

Reference： [1] Patent: WO2018/140513, 2018, A1, . Location in patent: Page/Page column 102
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 872

2
[ 50551-61-6 ]
[ 7168-85-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 10, p. 997 - 1001

3
[ 50551-61-6 ]
[ 952737-54-1 ]

Reference： [1] Patent: WO2018/140513, 2018, A1,

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Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 4h;
97%	Stage #1: 3-bromo-7-methoxy-2H-chromen-2-one With sodium hydroxide In ethanol at 79℃; for 0.0833333h; Microwave irradiation; Stage #2: With hydrogenchloride In water	5,6-Dimethoxy-3-methyl-benzofuran-2-carboxylic acid (2a) General procedure: 3-Bromo-4-methyl-6,7-dimethoxycoumarin (1a) (0.05 g, 0.167 mmol) was added to a microwave vessel. Ethanol (5 ml) and sodium hydroxide (0.0201 g, 0.503 mmol) were then added to the vessel that was then sealed and inserted into the microwave for 5 min, at 300 W and at a temperature of 79 °C with stirring. The reaction was monitored by thin layer chromatography (silica gel, 3:1 CH2Cl2/EtOAc). Upon completion of the reaction, the mixture was concentrated on a rotary evaporator and the resultant crude product obtained was dissolved in the minimum volume of water. This solution was acidified with concentrated hydrochloric acid to pH 1 resulting in precipitation of an off-white solid which was collected by vacuum filtration and dried in an oven at 80 °C to yield 3-methyl-5,6-dimethoxybenzofuran-2-carboxylic acid (2a, 0.039 g, 99%),
	With potassium hydroxide

Yield	Reaction Conditions	Operation in experiment
	With chloroform; phosphorus pentachloride
	With thionyl chloride for 1h; Heating;
	With phosphorus pentachloride In benzene for 2h; Heating;

	With thionyl chloride; N,N-dimethyl-formamide In toluene at 80℃;	4.1.2. 6-Methoxybenzofuran-2-carbonyl chloride (113) Compound 112 (1.92 g, 0.01 mol) and SOCl2 (2.8 mL, 0.04 mol)were dissolved in 50 mL of methylbenzene, and 2 drops of DMFwere added. The solution was stirred at 80 °C with a drying tubeattached to the apparatus. Then, the solution was evaporated todryness under reduced pressure, dissolved in pure methylbenzeneand evaporated to dryness again. Product 113 was immediatelyused for the next reaction.
	With thionyl chloride In toluene for 3h; Reflux;	4.1.1. General procedures for the synthesis of benzofuran-2- carboxamides 1b, 1c and 1d General procedure: Thionyl chloride (1.65 equiv) was added to a suspension of benzofuran-2-carboxylic acid derivatives (1 equiv) in anhydrous toluene (0.4 mmol/mL). After stirring the mixture for 3 h, at reflux, the reaction was cooled and concentrated. Then, the resulting benzofuran-2-carbonyl chloride derivative (1 equiv) was added in small portions to an ice-cold solution of 25% aq. NH4OH (0.5 mmol/ mL). Upon completion of the addition the reaction mixture was allowed to reach rt and a precipitate was formed. The solid was collected by filtration, washed with cold water and dried under vacuum.

Yield	Reaction Conditions	Operation in experiment
91%		To a stirred solution of Product of Step B (0.25 g, 1.21 mmol) in a mixture of THF, MeOH and H2O (5 ml : 2 ml : 1 ml), LiOH (0.145 g, 6 mmol) in H2O (0.5 ml) was added and the mixture was stirred for 3 h at room temp. The solvents were distilled off and the residue was portioned between EtOAc (20 ml) and 1 M HCI (2 ml). The organic layer was washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.21 g, 91 %), as a colourless solid. 1H-NMR (DMSO-de) 7.61 (d, 1 H, J = 8.67 Hz); 7.54 (s, 1 H); 7.24 (d, 1 H, J = 1 .59 Hz); 6.93 (dd, 1 H, J = 8.67, 2.4 Hz); 3.8 (s, 3H).
83%	With sodium hydroxide; In 1,4-dioxane; at 40℃; for 0.5h;	Compound 38 (1.1 g, 5 mmol)was dissolved in 20mL of dioxane,and 8.0 mL of 1 N NaOH was added. The solution initially becameturbid but clarified upon completion of the reaction after 30 min.The dioxane was removed by distillation under reduced pressure,and the remaining productwas dissolved inwater. The solutionwasmixed with dichloromethane and after stratification, the organicphase was discarded, and the aqueous phase was adjusted to pH = 3 with 10% HCl. The precipitate was collected and recrystallizedin dry methanol. Finally, 0.51 g (yield of 83%) of solid wasobtained. m.p: 195-196 C. 1H NMR (600 MHz, DMSO-d6) delta (ppm):3.84 (s, 3H), 6.97 (dd, J1=9.0 Hz, J2 = 1.8 Hz, 1H), 729 (d, J=1.8 Hz,1H), 7.59 (s, 1H), 7.64 (d, J= 9.0 Hz, 1H), 13.32 (s, 1H).
79%	With sodium hydroxide; In 1,4-dioxane; at 20℃; for 2h;	The ice bath condition 2- Hdroxyl ,-4- methoxybenzaldehyde,and anhydrous K2c03 ( 2.2g15.6mmo 1) Dissolved inDMF(30ml) slowlydripping bromo Ethylacetate(2.2g13mmo 1)drippingis finished 0C stirring , 30min, then at 60C oil bath reaction 12h Thereaction liquid is poured into the ice waterfilter chloroform soluble solidsanhydrousNa2s04 drying, filtration, rotary dry solvent silica gel column chromatographyseparation , get yellow solid 2.31g , 2.31g (yield as 80%), will it,soluble Dioxane,[20ml]added sodium hydroxide solution [12ml] normalatmospheric temperature stir 2Hours Dioxane steameddry, The remaining liquid is poured intoice water. use dichloromethanewashing adjustingPHValue to 2 filter collect solid1.64g (yield as 79%), dissolve it in dichloromethane (30ml)addedN.N Diisopropylcarbodiimide(DIC)(1.06g8.41mmol) normal atmospherictemperature stirring 1 hour after added ,-4-Dimethylaminopyridine (DMAP0.17g1.39mmo l) Diethyl(hydroxymethyl)phosphonate 1.44g,8.57mmo I)Heating reflux 6 hours after usewith full water and edible salt washingreaction solutionanhydrous magnesium sulphate dry filtering after steam drying, Ethyl acetatepetroleum ether system recrystallization obtainedproduct -6-methoxy benzofurane,-2-carboxylic acid (2?_Diethylphosphonatemethyl ester products 2.48g (yield for 85%).

[ CAS No. 50551-61-6 ]

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[ 50551-61-6 ] Synthesis Path-Upstream 1~3

[ 50551-61-6 ] Synthesis Path-Downstream 1~50