83790-87-8|(2-Butylbenzofuran-3-yl)(4-methoxyphenyl)methanone| Ambeed

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Quality Control of [ 83790-87-8 ] Purity: 97% SDS Specification

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Product Details of [ 83790-87-8 ]

CAS No. :	83790-87-8
Formula :	C₂₀H₂₀O₃
M.W :	308.37
SMILES Code :	O=C(C1=C(CCCC)OC2=CC=CC=C12)C3=CC=C(OC)C=C3
MDL No. :	MFCD11215603
InChI Key :	ZECBGDFBAKHQFF-UHFFFAOYSA-N
Pubchem ID :	3019323

Safety of [ 83790-87-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 83790-87-8 ]

* 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.

Downstream synthetic route of [ 83790-87-8 ]

[ 83790-87-8 ] Synthesis Path-Downstream 1~30

Yield	Reaction Conditions	Operation in experiment
71%	With aluminum (III) chloride; In dichloromethane; at 20℃; for 24h;	General procedure: To a dichloromethane solution (50 mL) of compound 2 (5.4 g, 24.83 mmol) was added 4-methoxybenzoyl chloride (4.4 mL, 32.28 mmol) and aluminum trichloride (3.3 g, 24.83 mmol). The mixture was stirred at room temperature for 24 hours. The reaction mixture was quenched with ice water and extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated to obtain a crude product, which was purified by silica gel column chromatography [petroleum ether/ethyl acetate=10:1] to obtain compound 3 (6.9 g, 78.9%) as a yellow solid.

2
[ 75-44-5 ]
[ 4265-27-4 ]
[ 75-34-3 ]
[ 83790-87-8 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With sodium hydrogencarbonate;aluminium chloride; In water; methoxybenzene;	EXAMPLE 1 Preparation of 2-n-butyl 3-(4-methoxy benzoyl) benzofuran 40 ml of anhydrous dichloroethane are placed in a reactor under argon and cooled to -20 C. Then 3 ml (41.87 mmoles) of phosgene, 2.5 ml (14.2 mmoles) of 2-n-butyl benzofuran and 2.13 g (15.96 mmoles) of aluminium chloride are successively introduced into the reactor. The solution is gradually heated to room temperature, stirred during 24 hours and cooled to -20 C. 1.55 ml (14.25 mmoles) of anisole are added and the solution is then heated to room temperature, stirred for 2 hours and poured into 100 ml of water. After 30 mn of vigorous stirring, the organic phase is separated, washed with 30 ml of a saturated solution of sodium bicarbonate, 40 ml of water then dried over sodium sulfate. After evaporation of the solvent and purification of the crude product obtained on a column of silica (eluant: methylene chloride/hexane 1/1), 3.44 g (11.17 mmoles) of 2-n-butyl 3-(4-methoxy benzoyl) benzofuran are obtained. Yield: 78.7%.

References: [1]Patent: US5266711,1993,A .

3
[ 83790-87-8 ]
[ 52490-15-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	aluminium chloride; In 1,1-dichloroethane; water;	a) 2-n-butyl 3-(4-hydroxy benzoyl) benzofuran To a solution of 2 g (6.5 mmoles) of 2-n-butyl 3-(4-methoxy benzoyl) benzofuran in 30 ml of dichloroethane 1.82 g (13.6 mmoles) of aluminium chloride are added under argon. The mixture is heated at reflux for 9 hours, then cooled to room temperature. The reaction mixture is then poured into 50 ml of water, stirred vigorously for 30 minutes, then the organic phase is separated. It is washed 3 times with 30 ml of water, dried over sodium sulfate and decolorized by means of diatomaceous earth. After evaporation of the solvent, 1.9 g (6.5 mmoles) of 2-n-butyl 3-(4-hydroxy benzoyl) benzofuran are obtained. Yield: 100% M.p.: 119-120 C.
91.6%	With aluminum (III) chloride; In chlorobenzene; at 80℃; for 2h;Inert atmosphere;	To a solution of compound 3 (1.9 g,5.46 mmol) in chlorobenzene (11 mL) was added AlCl3 (2.2 g, 16.38 mmol).The mixture was stirred at 80 C for 2 hours and was quenched with ice water(20 mL). The reaction mixture was extracted withEA (330 mL). The organicphase was dried over Na2SO4, filtered and concentrated togive the crude product, which was purified by flash chromatography [PE/EA=5:1]to give 4 (1.46g, 78.5%) asa yellow solid. 1H NMR (400 MHz, CDCl3)δ 8.32 (dd, J = 2.4, 0.5 Hz, 1H), 8.22 - 8.18 (m, 1H), 7.79 - 7.75 (m, 2H),7.55 (dd, J = 9.0, 0.5 Hz, 1H), 6.97 - 6.93 (m, 2H), 2.90 (dd, J = 8.1, 7.1 Hz,2H), 1.78 - 1.70 (m, 2H), 1.37 - 1.29 (m, 2H), 0.86 (t, J = 7.3 Hz, 3H).
Ca. 86.9%	With aluminum (III) chloride; In toluene; at 80 - 90℃;Large scale;	20.00 kg (64.9 mol, 1.0 eq) of compound 8 was added to 60.00 kg (3 w/w) of toluene.9.52 kg (71.4 mol, 1.1 eq) of aluminum trichloride was added and the reaction was carried out at 80 to 90 C for 2 to 4 hours.After the reaction, the reaction solution was transferred to 90.00 kg (4.5 w/w) of purified water.Adjust the pH to 2 with dilute hydrochloric acid, and wash the organic phase with 50.00 kg (2.5 w/w) of purified water twice.The organic phase was washed with 50.00 kg (2.5 w/w) saturated aqueous sodium chloride solution.It was dried by adding 2.00 kg (0.1 w/w) anhydrous sodium sulfate.The organic phase was concentrated under reduced pressure at 65 C until a solid precipitated, cooled to 0 C, and then allowed to crystallize for 4 hours.Vacuum filtration, wet drying at 80 C,A white crystalline powder of 16.60 kg (56.4 mol) of Compound 9 was obtained in a yield of about 86.9%.

55%	With sodium thioethylate; In N,N-dimethyl-formamide; at 110℃; for 16h;	In a RBF (100 mL) containing a SB, 86 (400 mg5 1.30 mmol) was diluted with DMF (18.0 mL) and NaSEt (0.426 g, 5.19 mmol) was added. The reaction mixture was heated to 110 C and stirred (16 h). The reaction was quenched by the addition of sat. NH4C1, and was extracted with EtOAc (4 x 25 mL). The combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo. The crude material was purified by column chromatography on Si02 (Hex: EtOAc; 4:1) to afford 87 (0.210 mg, 0.713 mmol, 55%) as a light yellow oil. 1H- NMR (400 MHz) CDC13: 7.81-7.78 (d, 2 H), 7.48-7.46 (d, 1 H), 7.37-7.36 (d, 1 H), 7.29-7.25 (m, 1 H), 7.20-7.16 (m, 1 H), 6.94-6.90 (d, 2 H), 6.56 (bs, 1 H), 2.93-2.89 (t, 2 H) 1.79-1.71 (m, 2 H), 1.38-1.32 (m, 2 H), 0.90-0.86 (t, 3 H); 13C-NMR (100 MHz) CDC13: 191.2, 165.0, 160.4, 153.6, 132.1, 131.6, 127.1 , 124.2, 123.4, 121.2, 1 16.7, 1 15.4, 1 1 1.0, 30.1, 27.9, 22.3, 13.7. LC/MS-MS: 295.0 121.2 m/z; GS1 and GS2 at 30, DP = 56, CE = 31 , CXP = 6, tR = 4.51 min.
82.3 g	With boron trifluoride diethyl etherate; In acetonitrile; at 80℃; for 2h;	110.9 g (0.36 mol) of 2-butyl-3- (4-methoxybenzoyl) benzofuran obtained in step (1) was charged into a reactor equipped with a magnetic stirrer,Boron trifluoride ether 10.2 g (72 mmol)Soluble in 2L acetonitrile;The mixture was stirred at 80 C for 2 hours,The organic phase is combined and then concentrated under reduced pressure; the recrystallization of ethyl acetate and ether is carried out to obtain the same as that of the ethyl acetate and the ethyl acetate solution,2-butyl-3- (4-hydroxybenzoyl) benzofuran82.3 g (0.28 mol).
8.16 g	With aluminum (III) chloride; In toluene; for 6h;Reflux;	Add to the 100 ml reaction bottle10.00 g of 2-butyl-(4-methoxybenzoyl)benzofuran,4.50 g of aluminum trichloride and 40 ml of toluene,The temperature was raised to reflux, and the reaction was kept for 6 hours, and the reaction was completed.Cool down to 0 C, pour into ice water, separate the liquid, extract the aqueous phase with toluene, and combine the organic phases.Add an equal volume of water, adjust the pH to above 12 with NaOH solution, and dispense.The aqueous phase is adjusted to pH less than 3 with hydrochloric acid and filtered.The filter cake was dried in vacuo to give a pale yellow solid, 8.16 g.

References: [1]Patent: US5266711,1993,A .
[2]Bioorganic and Medicinal Chemistry Letters,2021,vol. 46.
[3]Patent: CN109053652,2018,A .Location in patent: Paragraph 0019; 0055; 0061; 0064; 0070; 0079; 0081.
[4]Journal of Organic Chemistry,2019,vol. 84,p. 2941 - 2950.
[5]Patent: WO2012/48058,2012,A2 .Location in patent: Page/Page column 43.
[6]Patent: CN106946822,2017,A .Location in patent: Paragraph 0028; 0034; 0040; 0046-0047; 0052.
[7]Patent: CN109988131,2019,A .Location in patent: Paragraph 0015.

4
36%-hydrochloric acid [ No CAS ]
[ 4265-27-4 ]
[ 100-07-2 ]
[ 83790-87-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With iron(III) chloride; In water; toluene;	(a) 2-n-Butyl-3(-4-methoxybenzoyl)benzofuran Into a reactor were introduced 520 g (600 ml) of toluene and 174 g (1mol) of 2-n-butylbenzofuran. The mixture was heated to reflux, with stirring and the medium and the apparatus were dried by taking off a forerun, using a Dean Stark system. Approximately 35 g (about 40 ml) of toluene were removed by distillation in this manner. The reactor was cooled to room-temperature and 174 g (1.02 mol) of 4-methoxybenzoyl chloride were introduced rapidly in a single portion. The mixture was chilled to -10 C.+- 2 C. and 130 g (0.8 mol) of anhydrous ferric chloride were added, also rapidly and as a single portion. The reaction medium was maintained at -10 C.+- 2 C. for 15 minutes and was then allowed to return to room-temperature. The mixture was kept stirred for 6 hours and was once again chilled to about 0 C. After this operation, 200 g of purified water were then added gradually, without exceeding 20 C. After being kept at room-temperature for 30 minutes, the insoluble product (4-methoxybenzoic acid) was filtered off and was then rinsed on the filter with 90 g of toluene. The filtrates were collected in a separating funnel, the lower aqueous phase was separated off and the organic layer was washed with a solution of 30 g of 36%-hydrochloric acid in 200 g of purified water, and then with water until neutral. The organic phase was dried and the solvent was removed under vacuum until the mass reached a temperature of 80 C. under a residual pressure of about 50 mm Hg. In this manner, about 308 g of 2-n-butyl-3-(4-methoxy-benzoyl)-benzofuran were obtained in crude form. Yield:about 100%. The 2-n-butyl-3-(4-methoxybenzoyl)benzofuran obtained by this method had, on average, the following contents of impurities identified by thin-layer chromatography.
	With iron(III) chloride; In water; toluene;	(a) 2-n-Butyl-3-(4-methoxybenzoyl)benzofuran Into a reactor fitted with devices for stirring, adding reactants and with a condenser were introduced 174 g (1 mol) of 2-n-butylbenzofuran and 520 g of toluene. Traces of water were removed by azeotropic distillation. The mixture was cooled to 20 C. and 174 g (0.12 mol) of 4-methoxybenzoyl chloride were added rapidly. After cooling to -10 C., the medium was treated with 130 g of ferric chloride, added in a single portion. After 15 minutes at this temperature, the mixture was allowed to return to ambient temperature and was stirred for 6 hours at this temperature. The medium was hydrolyzed by the addition of 200 ml of water, the temperature not being allowed to exceed 20 C. After 15 minutes at this temperature, an insoluble product (4-methoxybenzoic acid) was filtered off, the filter was washed with toluene, and the aqueous phase was separated off. The organic phase was washed with a solution of 30 g of 36%-hydrochloric acid in 200 ml of water, and then with water until neutral, and was then dried. In this manner, a toluene solution containing about 308 g (about 100%) of 2-n-butyl-3-(4-methoxybenzoyl)benzofuran was obtained and was used as such.

References: [1]Patent: US4766223,1988,A .
[2]Patent: US4766223,1988,A .

5
C₃₁H₃₅O₃PolSi [ No CAS ]
[ 83790-87-8 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 6588 - 6589.

6
[ 4265-27-4 ]
[ 100-07-2 ]
[ 83790-87-8 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 81.2%	With aluminum (III) chloride; In 1,2-dichloro-ethane; at -20 - -10℃;Large scale;	10.70 kg (80.4 mol, 1.0 eq) of aluminum trichloride was added to 60.00 kg of 1,2-dichloroethane at -20 to -10 C.14.00 kg (80.4 mol, 1.0 eq) of compound 5 was added with stirring.After stirring uniformly, 16.46 kg (96.5 mol, 1.2 eq) of Compound 7 was added at -20 to -10 C, and the reaction was kept for 1 to 2 hours.After the reaction, the reaction solution was transferred to 90.00 kg of purified water, the pH was adjusted to 2 with dilute hydrochloric acid, and the organic phase was added and washed with 25.00 kg of purified water twice.The organic phase was washed with 45.00 kg of a saturated aqueous solution of sodium chloride and dried over 1.40 g of anhydrous sodium sulfate.The organic phase was concentrated under reduced pressure at 55 C.20.11 kg (65.0 mol) of compound 8 was obtained.The yield was about 81.2%.
71%	With aluminum (III) chloride; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	General procedure: To a solution of compound 2 (5.4 g, 24.83 mmol)and 4-methoxybenzoyl chloride (4.4 mL, 32.28 mmol) in DCM (50 mL) was added AlCl3(3.3 g, 24.83 mmol). The mixture was stirred at room temperature for 24hours and was quenchedwith ice water (50 mL). The reaction mixture was extractedwith DCM (350 mL). The organic phase was dried over Na2SO4,filtered and concentrated to give the crude product, which was purified byflash chromatography [PE/EA=10:1] to give 3 (6.9 g, 78.9%) as a yellowsolid.
64%		2-butylbenzofuran (400 mg, 0.405 mL, 2.30 mmol) was weighed out into a dry RBF (25 mL) containing a SB. The material was diluted in CS2 (6.0 mL), capped and a N2 balloon attached. The mixture was stirred and cooled in an ice bath (30 min). Next, 4-methoxybenzoyl chloride (0.404 mL, 2.98 mmol) was added followed by dropwise addition of tin (IV) chloride (0.370 mL, 2.98 mmol). The contents were stirred (3 h) at 0 C and slowly warmed to RT and stirred (3 d). The reaction mixture was diluted with ¾0 and extracted with EtOAc (4 x 12 mL). The combined organic layer was washed with HC1 (0.5 N), H20, sat. NaHC03, and brine. The organic layer was dried (Na2S0 ), filtered and concentrated in vacuo. The crude material was purified by column chromatography on Si02 (100% hexanes to 5% ethyl acetate in hexanes) to give 86 (0.455 g, 1.48 mmol, 64%) as a clear oil. -NMR (400 MHz) CDC13: 7.87-7.85 (d, 2 H), 7.49-7.47 (d, 1 H), 7.38-7.36 (d, 1 H), 7.28-7.25 (m, 1 H), 7.20-7.16 (m, 1 H), 6.97- 6.95 (d, 2 H), 3.88 (s, 3 H), 2.95-2.91 (t, 2 H) 1.79-1.75 (m, 2 H), 1.40-1.34 (m, 2 H), 0.92- 0.88 (t, 3 H); .3C-NMR (100 MHz) CDC13: 190.5, 164.6, 163.4, 153.6, 131.9, 131.7, 127.2, 124.1, 123.3, 121.2, 1 16.8, 113.7, 1 11.9, 55.5, 30.2, 27.8, 22.4, 13.7.

10.6 g

Add to the 100 ml reaction bottle5.50 grams of aluminum trichloride and24 ml of dichloromethane,Stir down to 0 C,Temperature control within 5 C to drop into it7.0 g of p-methoxybenzoyl chloride was stirred and allowed to stand for 1 hour after the completion of the dropwise addition.6.00 g of 2-butylbenzofuran was dissolved in 24 ml of dichloromethane, and the mixture was added dropwise to the above reaction liquid at a controlled temperature of 5 C. After the completion of the dropwise addition, the temperature was slowly raised to 25 C, and the reaction was kept for 2 hours, and the reaction was completed.After cooling to room temperature, pour into ice water, separate the liquid, and extract the aqueous phase with dichloromethane.Combine the organic layers and wash twice,The organic phase is concentrated under reduced pressure to give an oil10.60 grams.

References: [1]Patent: CN109053652,2018,A .Location in patent: Paragraph 0019; 0055; 0060; 0064; 0069; 0072; 0077; 0079.
[2]Bioorganic and Medicinal Chemistry Letters,2021,vol. 46.
[3]Patent: WO2012/48058,2012,A2 .Location in patent: Page/Page column 42-43.
[4]Patent: CN109988131,2019,A .Location in patent: Paragraph 0014.

7
[ 100-73-2 ]
[ 1137261-90-5 ]
[ 83790-87-8 ]

Yield	Reaction Conditions	Operation in experiment
110.9 g	With aluminum (III) chloride; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In toluene; at 100℃; for 1h;	A mixture of 1- (4-methoxyphenyl) -1,3-heptanedione (117.1 g, 0.5 mol)Acrolein dimer 112.0 g (1.0 mol)Dissolved in organic solvent toluene (2L)dibromo-5,5-dimethylhydantoin 142.9 g (0.5 mol),AlCl35.8 g (50 mmol),The reaction solution was stirred at 100 C for 1 hour in a reactor equipped with a magnetic stirrer.After the end of the reaction with saturated sodium bicarbonate and neutral reaction system to neutral; with ethyl acetate liquid - liquid extraction of the water phase; organic phase combined and concentrated under reduced pressure; ethyl acetate and ether recrystallization separation2-butyl-3- (4-methoxybenzoyl) benzofuran110.9 g (0.36 mol).

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 2941 - 2950.
[2]Patent: CN106946822,2017,A .Location in patent: Paragraph 0026; 0032; 0038; 0043-0044; 0050.

8
[ 90-02-8 ]
[ 83790-87-8 ]

References: [1]Patent: CN109053652,2018,A .
[2]Patent: CN109053652,2018,A .
[3]Patent: CN109053652,2018,A .

9
[ 5445-19-2 ]
[ 83790-87-8 ]

References: [1]Patent: CN109053652,2018,A .
[2]Patent: CN109053652,2018,A .
[3]Patent: CN109053652,2018,A .

10
[ 138320-26-0 ]
[ 83790-87-8 ]

References: [1]Patent: CN109053652,2018,A .
[2]Patent: CN109053652,2018,A .

11
C₁₆H₂₄O₅ [ No CAS ]
[ 83790-87-8 ]

References: [1]Patent: CN109053652,2018,A .

12
[ 138320-27-1 ]
[ 83790-87-8 ]

References: [1]Patent: CN109053652,2018,A .

13
[ 100-09-4 ]
[ 83790-87-8 ]

References: [1]Patent: CN109053652,2018,A .

14
[ 83790-87-8 ]
[ 1951-26-4 ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 2941 - 2950.
[2]Patent: CN109988131,2019,A .

15
[ 83790-87-8 ]
[ 1951-25-3 ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 2941 - 2950.

16
[ 100-06-1 ]
[ 83790-87-8 ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 2941 - 2950.

17
[ 624-24-8 ]
[ 83790-87-8 ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 2941 - 2950.

18
[ 533-58-4 ]
[ 83790-87-8 ]

References: [1]Patent: CN109988131,2019,A .

19
[ 693-02-7 ]
[ 83790-87-8 ]

References: [1]Patent: CN109988131,2019,A .

20
[ 83790-87-8 ]
[ 19774-82-4 ]