[ CAS No. 67475-56-3 ]

Name: 67475-56-3|5-Fluoro-2-methoxybenzene-1-sulfonyl chloride|98%
Brand: Ambeed
SKU: A120369
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Quality Control of [ 67475-56-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 67475-56-3 ]

CAS No. :	67475-56-3	MDL No. :	MFCD03618459
Formula :	C₇H₆ClFO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LUEBMKPHZDSPFH-UHFFFAOYSA-N
M.W :	224.64	Pubchem ID :	2783409
Synonyms :

Safety of [ 67475-56-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 67475-56-3 ]

* 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 [ 67475-56-3 ]
Downstream synthetic route of [ 67475-56-3 ]

[ 67475-56-3 ] Synthesis Path-Upstream 1~2

1
[ 459-60-9 ]
[ 67475-56-3 ]

Yield	Reaction Conditions	Operation in experiment
84.6%	at 0 - 20℃;	l-fluoro-4-methoxybenzene (10.0 g, 0.079mol) was added dropwise to sulfurochloridic acid (31.4ml, 0.474mol) at 0⁰C, The mixture was stirred at room temperature for about 6h, after which it was added dropwise into ice water. The mixture was extracted with CH₂Cl₂ three times. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo to give the title product (15.Og, 84.6percentyield).¹H NMR (300 MHz, DMSO-d⁶) δ 3.74 (s, 3H), 6.97 (dd, J= 4.3, 8.9 Hz, IH), 7.13 (dt, J= 3.4, 8.6 Hz, IH), 7.41 (dd, J= 3.3, 8.8 Hz, IH)
70%	With chlorosulfonic acid In dichloromethane at 0 - 5℃; for 3 h; Inert atmosphere	General procedure: A solution of the respective anisole (175 mmol) in CH2Cl2 (50 mL) was added dropwise to a 0 °C chlorosulfonic acid (100 mL) so as to maintain the reaction temperature below 5 °C. After the addition was complete, the reaction mixture was stirred for 3 h and poured over ice. The organic phase was separated, washes with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by short-path chromatography on silica gel using 10percent ethyl acetate in hexanes as eluent to provide the analytically pure target compound.
56%	at 25℃; for 3 h;	To a stirred CISO3H (50 mL) was added l-fiuoro-4-methoxy-benzene (10.0 g, 79.4 mmol) dropwise at 25°C. The mixture was stirred at this temperature for 3 hours. The mixture was poured into ice water (200 mL) and extracted with EtOAc (200 mL). The organic layer was wshed with brine (100 mL), dried over Na₂S0₄ and evaporated in vacuum to give 12 g of crude product. The crude was purifed by silica gel column chromatography (PE/EtOAc, 20/1) to give 10.0 g of 5-fluoro-2-methoxy-benzenesulfonyl chloride (yield: 56percent) as yellow oil

Reference： [1] Patent: WO2010/31, 2010, A1, . Location in patent: Page/Page column 86
[2] Tetrahedron, 2016, vol. 72, # 47, p. 7570 - 7578
[3] Patent: WO2013/126608, 2013, A1, . Location in patent: Paragraph 00812
[4] Patent: WO2005/18529, 2005, A2, . Location in patent: Page/Page column 54
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1735 - 1746
[6] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 1, p. 31 - 34
[7] Patent: WO2005/18529, 2005, A2, . Location in patent: Page/Page column 54

2
[ 371-41-5 ]
[ 67475-56-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1735 - 1746

[ 67475-56-3 ] Synthesis Path-Downstream 1~40

1
[ 14068-53-2 ]
[ 67475-56-3 ]
[ 67475-19-8 ]

Reference： [1]Pharmazie,1978,vol. 33,p. 254 - 256

2
[ 39223-04-6 ]
[ 67475-56-3 ]
[ 67475-26-7 ]

Reference： [1]Pharmazie,1978,vol. 33,p. 254 - 256

3
[ 27115-74-8 ]
[ 67475-56-3 ]
[ 67475-32-5 ]

Reference： [1]Pharmazie,1978,vol. 33,p. 254 - 256

4
[ 14068-54-3 ]
[ 67475-56-3 ]
[ 67475-39-2 ]

Reference： [1]Pharmazie,1978,vol. 33,p. 254 - 256

5
[ 52057-89-3 ]
[ 67475-56-3 ]
[ 67475-45-0 ]

Reference： [1]Pharmazie,1978,vol. 33,p. 254 - 256

6
[ 52057-90-6 ]
[ 67475-56-3 ]
[ 67475-51-8 ]

Reference： [1]Pharmazie,1978,vol. 33,p. 254 - 256

7
[ 870249-31-3 ]
[ 67475-56-3 ]
C₂₆H₃₆FN₃O₄S [ No CAS ]
C₂₆H₃₆FN₃O₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3292 - 3297

8
[ 885052-54-0 ]
[ 67475-56-3 ]
N-[2-(3,4-dichlorobenzenesulfonylamino)-phenyl]-5-fluoro-2-methoxybenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 20℃;	The monosulfonamide ( 1 mmol) obtained as above was dissolved in DCM (2 mL) and pyridine (2 mL). 5-fluoro-2-methoxy-benzenesulfonyl chloride (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (10 mX). The organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL), and brine (10 mL). The organic phase was dried over anhydroixs sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to give 302 mg of N-[2-(3,4- dichlorobenzenesulfonylamino)-phenyl]-5-fluoro-2-methoxybenzenesulfonamide. LC : T1- 1.19 min; MS: 505.5 (M+l)+; 1H KMR (DMSO-d6, 400 MHz): δ 3.92 (s, 3H), 6.85 (dd, IH),7.02 (m, IH), 7.08 (m, 2H), 7.28 (dd, IH), 7.40 (dd, .1H), 7.50 (m, IH), 7.56 (dd, IH), 7.80 (d, IH), 7.82 (s, IH), 9.11 (bs, IH), 9.56 (bs, IH) ppm

Reference： [1]Patent: WO2006/47302,2006,A1 .Location in patent: Page/Page column 69

9
[ 459-60-9 ]
[ 67475-56-3 ]

Yield	Reaction Conditions	Operation in experiment
84.6%	With chlorosulfonic acid; at 0 - 20℃;	l-fluoro-4-methoxybenzene (10.0 g, 0.079mol) was added dropwise to sulfurochloridic acid (31.4ml, 0.474mol) at 00C, The mixture was stirred at room temperature for about 6h, after which it was added dropwise into ice water. The mixture was extracted with CH2Cl2 three times. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo to give the title product (15.Og, 84.6%yield).1H NMR (300 MHz, DMSO-d6) δ 3.74 (s, 3H), 6.97 (dd, J= 4.3, 8.9 Hz, IH), 7.13 (dt, J= 3.4, 8.6 Hz, IH), 7.41 (dd, J= 3.3, 8.8 Hz, IH)
70%	With chlorosulfonic acid; In dichloromethane; at 0 - 5℃; for 3h;Inert atmosphere;	General procedure: A solution of the respective anisole (175 mmol) in CH2Cl2 (50 mL) was added dropwise to a 0 C chlorosulfonic acid (100 mL) so as to maintain the reaction temperature below 5 C. After the addition was complete, the reaction mixture was stirred for 3 h and poured over ice. The organic phase was separated, washes with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by short-path chromatography on silica gel using 10% ethyl acetate in hexanes as eluent to provide the analytically pure target compound.
56%	With chlorosulfonic acid; at 25℃; for 3h;	To a stirred CISO3H (50 mL) was added l-fiuoro-4-methoxy-benzene (10.0 g, 79.4 mmol) dropwise at 25C. The mixture was stirred at this temperature for 3 hours. The mixture was poured into ice water (200 mL) and extracted with EtOAc (200 mL). The organic layer was wshed with brine (100 mL), dried over Na2S04 and evaporated in vacuum to give 12 g of crude product. The crude was purifed by silica gel column chromatography (PE/EtOAc, 20/1) to give 10.0 g of 5-fluoro-2-methoxy-benzenesulfonyl chloride (yield: 56%) as yellow oil

	With chlorosulfonic acid; In chloroform; at 0 - 20℃; for 2h;	General procedure: The solution of 1-halo-4-alkoxybenzene 9 (8.5 g) in chloroform(50 mL) was introduced in a 250 mL three-necked flask, equippedwith a magnetic stirrer, a thermometer, a calcium chloride guardand a dropping reagent. The solution was cooled to 0 C and addeddropwise to chlorosulfonic acid (15 mL). After completion, thereaction mixture was heated to room temperature, left for 2 h,and then poured over crushed ice. The resulting mixture wasextracted with chloroform. The organic extracts were dried oversodium sulfate and concentrated under reduced pressure untilcrystallization. The resulting sulfonyl chlorides (7-8 g) (10a-c)were dissolved in 60 mL dioxane and added dropwise to a 30%m/v solution of ammonia (100 mL). The reaction mixture was concentratedunder reduced pressure, leading to a solid which wascollected by filtration, washed with cold water, and dried.
	With chlorosulfonic acid; at 20℃; for 2h;	4-Fluoroanisole (10. Og) was carefully added to chlorosulphonic acid (45. 81G) at 0C. The mixture was stirred at RT for 2h, then quenched with ice-water (500ML) and the solid filtered and dried, yield 16. 50g. 1H NMR: CDC13 : 8 7.72-7. 68 (1H, M), 7.44-7. 38 (1H, M) 7.12-7. 08 (1H, M), 4.05 (3H, s).

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 17574 - 17580
[2]Patent: WO2010/31,2010,A1 .Location in patent: Page/Page column 86
[3]Tetrahedron,2016,vol. 72,p. 7570 - 7578
[4]Patent: WO2013/126608,2013,A1 .Location in patent: Paragraph 00812
[5]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1735 - 1746
[6]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 31 - 34
[7]Patent: WO2005/18529,2005,A2 .Location in patent: Page/Page column 54

10
[ 1018652-50-0 ]
[ 67475-56-3 ]
[ 1425927-40-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap; In N,N-dimethyl-formamide; at 60℃; for 16h;	General procedure: This compound was prepared in a parallel synthesis format according to the following procedure.A 0.2 M solution of 6-amino-3-methyl-1 H-quinolin-2-one in anhydrous 1 :1 pyridine- DMF was prepared (Solution A). A 0.2 M solution of each sulfonyl chloride monomer, for example piperidine 1 -sulfonyl chloride, in anhydrous 1 :1 pyridine-DMF was likewise prepared. These sulfonyl chloride solutions were prepared freshly just before use. Solution A (500 uL, 100 umole) was added to each reaction vial, followed by 500 uL (1 equivalent, 100 umole) of sulfonyl chloride solution, with each sulfonyl chloride being unique to each vial in the library. Each vial was treated with 12 mg (100 umole) of DMAP, after which the vials were stirred for 16 h at 60 C. The reaction mixtures were evaporated in a Thermo Explorer (2 hr, 5 torr, at 45 C). Each of the crude products was dissolved in 1 ml_ of DMSO. 10 μΙ_ of the DMSO solution was diluted to 200 μΙ_ with DMSO for QC analysis and the remaining amount was submitted for prep-HPLC purification on a WatersAutopurification System using a gradient of 0.05% formic acid in water and acetonitrile. Product fractions were evaporated to dryness and weighed. For 74: Calculated molecular weight 362.07; found MH+ 363.16.

Reference： [1]Patent: WO2013/27168,2013,A1 .Location in patent: Page/Page column 59

11
[ 462-08-8 ]
[ 67475-56-3 ]
[ 893669-16-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With triethylamine; In tetrahydrofuran; at 20℃;	The mixture of 5-fluoro-2-methoxy-benzenesulfonyl chloride (3 g, 13.4 mmol), pyridine-3-ylamine (1.89 g, 13.3 mmol), TEA (2.7 g, 26.7 mmol) in anhydrous THF (30 mL) was stirred at room temperature overnight. To the mixture was added water (50 mL). The mixture was extracted with EtOAc (50 mL x3). The organic layer was dried over Na2S04. The solution was concentrated to dryness and the residue solid was re-crystallized from DCM to give 2.3 g (yield: 52%>) of 5-fluoro-2-methoxy-N-pyridin-3-yl-benzenesulfonamide as yellow solid. [00814] 1H NMR (DMSO-<, 400 MHz): δ = 10.45 (1H, brs), 8.31 (1H, d), 8.22 (1H, dd), 7.55 (1H, dd), 7.47 -7.51 (2H, m), 7.19-7.29 (2H, m), 3.85 (3H, s). MS: m/z 283.0 (M+H+).

Reference： [1]Patent: WO2013/126608,2013,A1 .Location in patent: Paragraph 00813-00814

12
[ 371-41-5 ]
[ 67475-56-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1735 - 1746

13
[ 67475-56-3 ]
[ 444-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In 1,4-dioxane;	General procedure: The solution of 1-halo-4-alkoxybenzene 9 (8.5 g) in chloroform(50 mL) was introduced in a 250 mL three-necked flask, equippedwith a magnetic stirrer, a thermometer, a calcium chloride guardand a dropping reagent. The solution was cooled to 0 C and addeddropwise to chlorosulfonic acid (15 mL). After completion, thereaction mixture was heated to room temperature, left for 2 h,and then poured over crushed ice. The resulting mixture wasextracted with chloroform. The organic extracts were dried oversodium sulfate and concentrated under reduced pressure untilcrystallization. The resulting sulfonyl chlorides (7-8 g) (10a-c)were dissolved in 60 mL dioxane and added dropwise to a 30%m/v solution of ammonia (100 mL). The reaction mixture was concentratedunder reduced pressure, leading to a solid which wascollected by filtration, washed with cold water, and dried.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1735 - 1746

14
[ 67475-56-3 ]
N-isopropyl-N'-(5-fluoro-2-methoxybenzenesulfonyl)urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1735 - 1746

15
[ 67475-56-3 ]
N-isopropyl-N'-(5-fluoro-2-methoxybenzenesulfonyl)thiourea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1735 - 1746

16
[ 67475-56-3 ]
N-ethyl-5-fluoro-2-hydroxybenzenesulfonamide [ No CAS ]