[ CAS No. 17213-57-9 ] {[proInfo.proName]}

Name: 17213-57-9|3,5-Dimethoxybenzoyl chloride|98%
Brand: Ambeed
SKU: A585835
Price: 8.0 USD
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 17213-57-9 ]

CAS No. :	17213-57-9	MDL No. :	MFCD00000676
Formula :	C₉H₉ClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FTHPLWDYWAKYCY-UHFFFAOYSA-N
M.W :	200.62	Pubchem ID :	87003
Synonyms :

Calculated chemistry of [ 17213-57-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.61
TPSA :	35.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.33
Log Po/w (XLOGP3) :	3.17
Log Po/w (WLOGP) :	2.08
Log Po/w (MLOGP) :	1.4
Log Po/w (SILICOS-IT) :	2.35
Consensus Log Po/w :	2.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.22
Solubility :	0.12 mg/ml ; 0.000596 mol/l
Class :	Soluble
Log S (Ali) :	-3.59
Solubility :	0.0519 mg/ml ; 0.000259 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.22
Solubility :	0.12 mg/ml ; 0.0006 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 17213-57-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 17213-57-9 ]

* 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 [ 17213-57-9 ]
Downstream synthetic route of [ 17213-57-9 ]

[ 17213-57-9 ] Synthesis Path-Upstream 1~6

1
[ 17213-57-9 ]
[ 20469-65-2 ]

Reference： [1] European Journal of Organic Chemistry, 1998, # 2, p. 359 - 364

2
[ 17213-57-9 ]
[ 877-88-3 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2004, vol. 47, # 3, p. 167 - 174

3
[ 17213-57-9 ]
[ 25245-27-6 ]

Reference： [1] Patent: CN107840792, 2018, A,

4
[ 17213-57-9 ]
[ 65976-77-4 ]

Reference： [1] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 246,249

5
[ 17213-57-9 ]
[ 52189-63-6 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666

6
[ 17213-57-9 ]
[ 75996-29-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666

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Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 4h;	General procedure: Dimethylformamide (1 drop) and SOCl2 were added to a solution of the corresponding acid inTHF, and the reaction mixture was stirred at room temperature for 30 min. Then, the mixture was heated to 50°C and stirred at this temperature for 4 h. After the complete conversion of the starting acid, the solvent was evaporated, and the product was used without further purification.
99%	With thionyl chloride In N,N-dimethyl-formamide for 18h; Heating;
89%	With oxalyl dichloride In benzene 2 h, room t., 1 h, reflux;

87%	With pyridine; thionyl chloride In tetrahydrofuran
83.6%	With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 8h; Large scale;	2 Example 2: Preparation of 3,5-dimethoxybenzoyl chloride: Add 1821 mg of 3,5-dimethoxybenzoic acid to the reactor. Add 40 ml of tetrahydrofuran and stir. 0.5 ml of N,N-dimethylformamide was added at room temperature, followed by stirring at room temperature for 0.5 hour, and 3 g of thionyl chloride was added dropwise, followed by stirring at room temperature for 8 hours. After completion of the reaction, the compound 3,5-dimethoxybenzoyl chloride was obtained by post-treatment and purification, and the yield was 83.6%.
	With phosphorus(V) chloride
	With carbon disulfide; phosphorus(V) chloride
	With phosphorus(V) chloride
	With thionyl chloride
	With thionyl chloride In tetrahydrofuran for 2h; Heating;
	With thionyl chloride for 4h; Heating;
	With thionyl chloride for 0.5h; Heating;
	With thionyl chloride; N,N-dimethyl-formamide In toluene at 60 - 70℃;
	With thionyl chloride In benzene at 1℃; for 1h; Heating;
	With thionyl chloride In chloroform Heating;
	With phosphorus(V) chloride In benzene at 60℃; for 4h;
	With thionyl chloride In benzene at 80℃; for 3h;
	With thionyl chloride for 1h; Heating;
	With thionyl chloride In benzene at 80℃; for 3h;
	With thionyl chloride In benzene at 80℃; for 3h;
	With thionyl chloride Heating;
	With thionyl chloride In toluene at 70℃; for 2h;
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide for 1h; Heating;
	With trichloroacetonitrile; triphenylphosphine In dichloromethane at 20℃; for 1h;
	With thionyl chloride for 2h; Heating;
	With thionyl chloride In <i>N</i>-methyl-acetamide; toluene	30 EXAMPLE 30 The starting material can be manufactured as follows: 72.9 g of 3,5-dimethoxybenzoic acid are suspended in 320 ml of toluene, and 2 drops of dimethylformamide are added thereto. The suspension is heated to 50°. 40 ml of thionyl chloride are added dropwise at that temperature within a period of 10 minutes. The whole is then heated to 90° (vigorous evolution of gas) and stirred for 2 hours. The reaction mixture is cooled and concentrated by evaporation in a rotary evaporator. After the addition of toluene, the whole is again concentrated by evaporation. The oily residue is dried for 15 minutes under a high vacuum. 3,5-dimethoxybenzoyl chloride is thus obtained.
	With thionyl chloride In dichloromethane at 20℃; for 16h;
	With thionyl chloride In dichloromethane at 42℃; for 2h;	5 3-(3,5-Dimethoxybenzamido)cyclohexanecarboxylic acid. A mixture of 3- (3,5-dimethoxybenzamido)-cyclohexanecarboxylic acid (1.47 g, 8.07 mmol), thionyl chloride (0.71 ml, 9.7 mmol), DMF (0.03 ml, 0.38 mmol), and DCM (15 ml) was stirred at 420C for 2 hours, after which it was concentrated in vacuum and dried in high vacuum. A solution of the obtained solid in 10 ml of THF was added to a stirred mixture of 3- aminocyclohexanecarboxylic acid (1.26 g, 8.8 mmol), thriethylamine (3.3 ml, 24 mmol), THF (15 ml), and water (15 ml) at O0C in 5 min. The stiriing continued for 1 hour at the same temperature and for 3 hours at room temperature. After this, 10 ml of 2 M aqueous hydrochloric acid was added. The mixture was extracted with 30 ml of ethyl acetate. A precipitate appeared on standing. The extract was concentrated to dryness and dried in high vacuum to obtain 2.3 g (93%) of the target product as a white solid.
	With thionyl chloride for 2h; Reflux;
	With thionyl chloride In dichloromethane at 22℃;
	With thionyl chloride Reflux;
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 45℃; for 5h;
	With thionyl chloride Reflux;	5.1.5. General procedures for benzoyl chloride (6a-6m) General procedure: The selected acid was refluxed in thionyl chloride for 2-3 h, and then the solution was cooled to room temperature, and the remaining thionyl chloride was evaporated to afford the acyl chloride, which was used without further purification.
	With thionyl chloride for 2h; Reflux;
	With oxalyl dichloride
	With thionyl chloride for 0.5h; Reflux;	3 Ethyl 3-(3,5-dimethoxyphenyl)-3-oxopropanoate A solution of 3,5-dimethoxybenzoic acid (5 g, 27.47 mmol, 1.00 equiv) in thionyl chloride (40 mL) was stirred at reflux for 30 minutes, then concentrated in vacuo to afford 3,5-dimethoxybenzoyl chloride as a yellow oil. Separately, a mixture of potassium 3-ethoxy-3-oxopropanoate (9.3 g, 54.71 mmol, 1.99 equiv), MgCl2 (6.5 g, 68.42 mmol, 2.49 equiv) and triethylamine (5.5 g, 54.46 mmol, 1.98 equiv) in CH3CN (60 mL) was stirred at 30° C. for 30 minutes. The solution of 3,5-dimethoxybenzoyl chloride in CH3CN (40 mL) was added dropwise, followed by the addition of triethylamine (550 mg, 5.45 mmol, 0.20 equiv). The resulting solution was stirred at 30° C. overnight, then diluted with 100 mL EtOAc and washed with 100 mL 1N hydrochloric acid and 100 mL brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether (1:20)). This resulted in 1.7 g (23%) of ethyl 3-(3,5-dimethoxyphenyl)-3-oxopropanoate as a red solid. LC-MS: (ES, m/z): 253 [M+H]+
	With thionyl chloride at 75℃; for 6h; Inert atmosphere;	General procedure for the preparation of 3m-3p General procedure: The mixture of suitable substituted benzoic acid (5a-5d, 0.01 mol) and thionyl chloride (5 ml) was stirred at 75 °C for 6 h under nitrogen. After removal of excess thionyl chloride in vacuo, 4-methoxy-2-nitroaniline (1b, 0.01 mol) and anhydrous Na2CO3 (0.1 mol) were added to the reaction mixture dissolved in anhydrous acetone (50 ml). After stirring at 54 °C for 1 h, the solvent was removed under vacuum and the residue was poured into ice water with stirring. The precipitated solid was fitered, washed with ice water and dried to obtain the corresponding N-phenylbenzamide derivatives (7a-7d). To a solution of N-phenylbenzamide derivatives (7a-7d, 0.01 mol) in anhydrous acetic acid (50 ml) was added iron powder (0.03 mol), and then the mixture was refluxed at 100 °C. After completion of the reaction as indicated by TLC, the solvent was evaporated under reduced pressure and the residue was extracted with CH2Cl2 (3 × 20 mL). The combined organic fractions were washed with saturated NaHCO3, brine, dried (Na2SO4), and evaporated in vacuo. The residue was chromatographed on silica gel using petroleum ether/EtOAc (10:1-4:1).
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane	4.2.28 General benzanilide synthesis, Method A General procedure: The benzoyl chloride was prepared by stirring benzoic acid (1.0 mmol) with SOCl2 (0.363 mL, 5.0 mmol) and DMF (1 drop) in CH2Cl2 (5 ml) for overnight and evaporating the volatile materials under reduced pressure. To the solution of benzoyl chloride in CH2Cl2 (5mL) were added an aniline (1.0 mmol) and DIEA (0.871 mL, 5.0 mmol), and the reaction was stirred until no starting material by TLC (1-24 h) at room temperature. After dilution with CH2Cl2 (30mL), the organic layer was washed with brine (40 mL), dried with anhydrous MgSO4, and evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography to obtain a benzanilide.
	With phosphorus(V) chloride
	With thionyl chloride Inert atmosphere; Schlenk technique;
	With oxalyl dichloride; N,N-dimethyl-formamide In chloroform at 20℃;	2.3.1. General procedure for syntheses of benzoylferrocene derivatives General procedure: A mixture of 10.0 mmol benzoic acid derivatives 1, 50.0 mL chloroform, 1 to 2 drops of DMF as catalyst, and oxalyl chloride (1.90 g, 15.0 mmol) was stirred at room temperature for 3.0-4.0 h. The solvent and excess oxalyl chloride were removed by rotary evaporation to produce crude benzoyl chloride derivatives 2.
	With thionyl chloride for 6h; Reflux;
	With thionyl chloride Reflux;
	With oxalyl dichloride In tetrahydrofuran at 0 - 5℃;
	With thionyl chloride at 80℃; for 4h;
	With thionyl chloride In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;
	With thionyl chloride; N,N-dimethyl-formamide In toluene at 100℃; for 6h;	2 Synthesis of 3,5-dimethoxybenzoyl chloride [1] To a suspension of 3,5-dimethoxybenzoic acid (95 g, 521 mmol) in toluene (dry, 950 mL) was added thionyl chloride (74.4 g, 626 mmol, 45.4 ml) and a catalytic amount of DMF (0.2 mL). The mixture was heated to 100° C. and stirred for 6 hours. A clear solution was formed. The mixture was allowed to cool to room temperature and all volatiles evaporated in vacuo using a rotary evaporatot The mixture was stripped twice with fresh toluene (2x100 mL). Yield:flOg of a brown oil (105% yield).
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h;
	With thionyl chloride Reflux;	Step 1. 3,5-dimethoxybenzoyl chloride 3,5-dimethoxybenzoic acid (27.3 g, 150 mmol, compound 1) was suspended in 120 mL thionylchloride, and the mixture was heated and held at reflux until 1 dissolved. Then, thionyl chloridewas evaporated under reduced pressure conditions and the residue was diluted with 150 mLanhydrous acetonitrile.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	General procedure for the synthesis of 4-hydroxy-ynone (2) General procedure: To a stirred solution of 200 mg acid in 5 cm3, drydichloromethane oxalyl chloride (1.5 equiv.) was addeddropwise under nitrogen atmosphere at 0 C during which the colour of the solution changes to black. After 6 h,solvent was removed under reduced pressure and the soformedacid chloride was used for the next reaction withoutfurther purification.
11 g	With thionyl chloride at 90℃; for 2h;	1 (1)Synthesis of 12 In a 500 mL (ml) round bottom flask was added 3,5-dimethoxybenzoic acid (10.0 g (g),55mmol (mole)),Then add 50 mL of thionyl chloride to dissolve it.Heat at 90 ° C (degrees Celsius) for 2 h (hours) (TLC (Thin Layer Chromatography) tracking). After the reaction is over,The thionyl chloride was evaporated to dryness under reduced pressure at 60 ° C to afford 12 11 g of brown oily material.Go directly to the next step.
	With thionyl chloride In dichloromethane for 3h; Reflux;	General Procedure for Synthesis of Compounds (2a-2c) General procedure: To a mixture of benzoic acid 3,4,5-trimethoxybenzoic acid (2.0 g, 9.43 mmol, 1.0 eq.) and SOCl2 (4.48 g, 37.70 mmol, 4.0 eq.) in anhydrous dichloromethane (10 mL), After refluxing for 3h, the reaction mixture was concentrated in vacuo to afford compound 2a (2.2 g, 100%) as white solid.
	With thionyl chloride for 3h; Reflux;
	With oxalyl dichloride
	With thionyl chloride In benzene at 80℃; for 3h;	General procedure: The synthesis of all benzamide derivatives were done by using the method shown on the literature [24]. Suitable benzoic acid (0.5 mmol) with thionyl chloride (1.5 ml) were refluxed at 80 °C in benzene (5 ml) for 3 h. Afterwards, the excess thionyl chloride was evaporated in vacuo. Then, the residue was solved in ether (10 ml). This solution added during 1 h to a stirred, ice-cold mixture of suitable o-aminophenol (2-amino-(4 or 5)-nitrophenol) (0.5 mmol), water (10 ml), diethyl ether(10 ml), and sodium bicarbonate (0.5 mmol). The mixture was kept stirred at the room temperature overnight, then filtered. After wards the residue was washed by using water, 2N HCl, water, and ether, respectively, and finally benzamide derivatives were achieved (Scheme 1). The obtained crude benzamides were recrystallized using the ethanol in order to purify. All of the obtained crystals were dried in vacuo. Physical and spectral datas of the newly synthesized benzamides were reported below (see also Supplementary Information 1).
	With thionyl chloride
	With oxalyl dichloride at 0 - 20℃;	2.1 General procedure for the preparation of benzamides 1a-1ac ^1-2 General procedure: Acid chloride (20 mol) was prepared from the corresponding carboxylic acid and oxalyl chloride. Acid chloride was added to a solution of 2,3,4,5,6-pentafluoroaniline (22 mmol) in toluene (50 mL). The reaction mixture was stirred for 24 h under reflux. After cooling to room temperature, the precipitate was filtered off, washed with water, and recrystallized from toluene or ethyl acetate/hexane to give the products 1 (the crude mixture was sometimes purified by flash chromatography if necessary).
	With oxalyl dichloride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	General procedure for preparation of benzoyl chlorides 2a-w. General procedure: To the solution of benzoic acids (2.4 mmol) in anhydrous THF(10 mL) under nitrogen atmosphere at 0 C was slowly added oxalylchloride (3.6 mmol). The reaction mixture was then stirred for 2-3 h under nitrogen. The reaction mixture was changed from transparent to a slightly yellowish color. The solvent was evaporatedon vacuo rotavapor, and the obtained product was directly used for the next reaction.
	With thionyl chloride Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;	Acyl chlorides General procedure: The acid (5 mmol) was dissolved in anhydrous CH2Cl2 (10 mL) and DMF (a few drops) added.Oxalyl chloride (6 mmol, 1.2 equiv.) was added dropwise to the solution, that was cooled in an icewater bath. The resulting mixture was allowed to stir at room temperature for an additional 4 h andthe solvent was evaporated to afford the crude acyl chloride, which was used directly in the nextstep.
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
50%	In hexane; dichloromethane; ethyl acetate	4.6 3,5-Dimethoxybenzoyl chloride (5.19 g, 25.87 mmol), 1,2,3-trimethoxybenzene (4.35 g, 25.87 mmol) in anhydrous methylene chloride (40 ml), and aluminum chloride (3.79 g, 28.45 mmol) were treated in the same manner as described above for the synthesis of (2,5-dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone. The crude material was purified via flash column chromatography (20% EtOAc in hexane) to give (3,5-dimethoxy-phenyl)-(2-hydroxy-3,4-dimethoxy-phenyl)-methanone as a yellow solid (4.15 g, 50%); 1H-NMR (CDCl3) δ 12.36 (s, 1H, OH), 7.42 (d, J=9 Hz, 1H, Ar), 6.75 (d, J=2 Hz, 2H, Ar), 6.64 (t, J=2 Hz, 1H, Ar), 6.47 (d, J=9 Hz, 1H, Ar), 3.94 (s, 6H, 2OCH3), 3.84 (s, 6H, 2OCH3); 13C NMR (CDCl3) δ 200.4, 160.7, 158.9, 158.0, 140.1, 136.9, 130.3, 114.6, 107.0, 103.8, 102.9, 60.9, 56.3, 55.7; Anal. Calcd. For C17H8O6: C, 64.14; H, 5.70. Found: C, 64.29; H, 5.42; N, <0.05.
	With carbon disulfide; aluminium trichloride

Yield	Reaction Conditions	Operation in experiment
78.4%	With ammonium hydroxide In acetonitrile at 20℃; for 1.5h; Cooling with ice;	2 (2) Synthesis of 13 Add 50 mL of ammonia water to a 500 mL round bottom flask, ice bath for 20 minutes, and slowly dissolve 12 (11.0 g, 55 mmol) in 50 mL of acetonitrile into a three-necked flask, during which a large amount of white solid was produced, and the reaction was carried out at room temperature for 1.5 h ( TLC tracking). After the reaction was completed, the mixture was transferred to a round-bottomed flask, and the acetonitrile was evaporated to dryness, and the white solid was washed with 200 ml of water, filtered, and dried in vacuo to give a white powdery solid 13 7.8 g, yield 78.4%
	With ammonia
	With ammonia In tetrahydrofuran at 0℃;

[ CAS No. 17213-57-9 ] {[proInfo.proName]}

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Physicochemical Properties

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Application In Synthesis of [ 17213-57-9 ]

[ 17213-57-9 ] Synthesis Path-Upstream 1~6

[ 17213-57-9 ] Synthesis Path-Downstream 1~46

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Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In dichloromethane
	In dichloromethane; water	1 Synthesis of 3-(3-,5--dimethoxybenzoyl)-2-(4--methoxyphenyl)-6-methoxybenzo[b]thiophene Synthesis of 3-(3-,5--dimethoxybenzoyl)-2-(4--methoxyphenyl)-6-methoxybenzo[b]thiophene To a well-stirred solution of 2-(4--methoxyphenyl)-6-methoxybenzo[b]thiophene (0.615 g, 2.27 mmol) and 3,5-dimethoxybenzoyl chloride (1.37 g, 6.83 mmol) in CH2 Cl2 (45 mL) was added AlCl3 (1.21 g, 9.09 mmol) portion-wise over a 15 minute period. After 17 hours, water was added, and the product was isolated initially by extraction with CH2 Cl2 and subsequently by extraction with EtOAc. The organic layers were separately washed with brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 60:40 EtOAc/hexane) afforded the title compound (0.475 g, 1.09 mmol, 48%) as an off-white solid. Recrystallization (hexane/ethanol) afforded a highly pure, crystalline sample with mp 114°-120° C.: 1 H-NMR (CDCl3, 360 Mhz): δ=7.59 (d,J=8.9 Hz, 1H, ArH), 7.32 (d,J=8.5 Hz, 2H, ArH), 7.32 (d,J=2.4 Hz, 1H, ArH), 6.98 (dd,J=9.0,2.4 Hz, 1H, ArH), 6.94 (d,J=2.1 Hz, 2H, ArH), 6.76 (d,J=8.7 Hz, 2H, ArH), 6.52 (t,J=2.4 Hz, 1H, ArH), 3.89 (s,3H, --OCH3), 3.76 (s,3H, --OCH3), 3.71 (s,6H, --OCH3); 13 C-NMR (CDCl3, 90 Mhz): δ=194.0, 160.5, 159.8, 157.7, 143.9, 140.0, 139.3, 133.8, 130.3, 130.1, 126.0, 124.1, 114.9, 114.0, 107.6, 106.1, 104.4, 55.6, 55.5, 55.2. HRMS (EI) M+ calcd for C25 H22 O5 S 434.1188, found 434.1245.
	In dichloromethane for 17h;	1 Synthesis of 3-(3',5'-dimethoxybenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene To a well-stirred solution of 2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene (0.615 g, 2.27 mmol) and 3,5-dimethoxybenzoyl chloride (1.37 g, 6.83 mmol) in CH2Cl2 (45 mL) was added AlCl3 (1.21 g, 9.09 mmol) portion-wise over a 15 minute period. After 17 hours, water was added, and the product was isolated initially by extraction with CH2Cl2 and subsequently by extraction with EtOAc. The organic layers were separately washed with brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 60:40 EtOAc/hexane) afforded the title compound (0.475 g, 1.09 mmol, 48%) as an off-white solid. Recrystallization (hexane/ethanol) afforded a highly pure, crystalline sample with mp 114-120° C.: 1H-NMR (CDCl3, 360 Mhz): δ=7.59 (d, J=8.9 Hz, 1H, ArH), 7.32 (d, J=8.5 Hz, 2H, ArH), 7.32 (d, J=2.4 Hz, 1H, ArH), 6.98 (dd, J=9.0, 2.4 Hz, 1H, ArH), 6.94 (d, J=2.1 Hz, 2H, ArH), 6.76 (d, J=8.7 Hz, 2H, ArH), 6.52 (t, J=2.4 Hz, 1H, ArH), 3.89 (s, 3H, -OCH3), 3.76 (s, 3H, -OCH3), 3.71 (s, 6H, -OCH3); 13C-NMR (CDCl3, 90 Mhz): δ=194.0, 160.5, 159.8, 157.7, 143.9, 140.0, 139.3, 133.8, 130.3, 130.1, 126.0, 124.1, 114.9, 114.0, 107.6, 106.1, 104.4, 55.6, 55.5, 55.2. HRMS (EI) M+ calcd for C25H22O5S 434.1188, found 434.1245. Anal. Calcd. for C25H22O5S: C, 69.11; H, 5.10; S, 7.38. Found: C, 69.00; H, 5.16; S, 7.34.

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2) Ag₂O, H₂O / 1) Et₂O 2: 98 percent / LiAlH₄ / tetrahydrofuran / Heating
	Multi-step reaction with 3 steps 1: diethyl ether 2: Ag₂O 3: LiAlH₄

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In dichloromethane at 20℃; for 5h;	10.I Step I, Preparation of 3-bromopropyl-3,5-dimethoxybenzoate (Intermediate 1-3) Weigh 3,5-dimethoxybenzoyl chloride (Intermediate 1-1) (2g, 10mmol) and 3-bromo-1-propanol (Intermediate 1-2) (1.07mL, 5mmol), Dissolve in 20 mL of dichloromethane, stir to dissolve, then slowly add triethylamine (1.5 mL, 15 mmol) dropwise, and stir at room temperature. The reaction process is monitored by TLC. The reaction is complete after about 5 hours. After adding 20 mL of ultrapure water to quench the reaction, adding 20 mL of dichloromethane for extraction, washing with saturated NaCl solution 3 times, drying the dichloromethane layer with anhydrous MgSO4, filtering, removing by rotary evaporation and concentrating to obtain the crude product, silica gel column Chromatographic purification to obtain colorless oily liquid intermediate 1-3, yield: 80%.
69%	With triethylamine In dichloromethane Inert atmosphere;	3-Bromopropyl 3,4,5-trimethoxybenzoate (1) General procedure: To a solution of 3.5 g 3,4,5-trimethoxybenzoyl chloride (15.2 mmol) in 25 mL of CH2Cl2 is added 5 mL of triethylamine and 1.5 mL (16.7 mmol) 3-bromo-1-propanol and the mixture was stirred overnight. The reaction is rinsed with water, dried (MgSO4), filtered and chromagraphed with 25% EtOAc in hexane to isolate 3.57 g of white solid (71%).

Yield	Reaction Conditions	Operation in experiment
21%	With aluminum (III) chloride In 1,2-dichloro-ethane at 110℃; for 0.0333333h; Microwave irradiation; Sealed tube;
21%	With aluminum (III) chloride In 1,2-dichloro-ethane at 25 - 100℃; for 0.05h; Microwave irradiation; Sealed tube;

Yield	Reaction Conditions	Operation in experiment
36%	With triethylamine; In dichloromethane; at 20℃;Cooling with ice;	Take a 100ml single bottle,Add 10ml of anhydrous methylene chloride,0.17g of triethylamine and 0.1g of p-hydroxyphenylpiperazine,Stir to dissolveA 0.16 g solution of 3,5-dimethoxybenzoyl chloride dissolved in dichloromethane was added dropwise on an ice bath.Stir at room temperature overnight. After the reaction is complete, add water to quench.Dichloromethane extraction, drying over anhydrous sodium sulfate, and concentration.Column chromatography gave the target compound 3m 0.07 g (36%).
36%	With triethylamine; In dichloromethane; at 0 - 20℃;	General procedure: To a mixture of Methyl 2-aminothiophene-3-carboxylate (0.1 g, 636.18 umol, 1.0 eq.) and triethylamine (0.19 g, 1.91 mmol, 3.0 eq.) in anhydrous dichloromethane (10 mL), 3,4,5-Trimethoxybenzoyl chloride 2a (0.22 g, 954.28 umol,1.5 eq.) in dichloromethane was slowly added at 0 C. After stirring at r.t overnight, the reaction mixture was diluted with water (3×10 mL), and the resulting mixture was extracted with dichloromethane. The organic layer was washed with water and brine, then dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography to afford compound 3a.

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