[ CAS No. 7205-98-3 ] {[proInfo.proName]}

Name: 7205-98-3|((Chloromethyl)sulfonyl)benzene|98%
Brand: Ambeed
SKU: A203127
Price: 33.0 USD
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2D 3D

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Quality Control of [ 7205-98-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7205-98-3 ]

SDS Specification

Alternatived Products of [ 7205-98-3 ]

Product Details of [ 7205-98-3 ]

CAS No. :	7205-98-3	MDL No. :	MFCD00007551
Formula :	C₇H₇ClO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NXAIQSVCXQZNRY-UHFFFAOYSA-N
M.W :	190.65	Pubchem ID :	81625
Synonyms :

Calculated chemistry of [ 7205-98-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.33
TPSA :	42.52 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) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	1.24
Log Po/w (WLOGP) :	2.74
Log Po/w (MLOGP) :	1.85
Log Po/w (SILICOS-IT) :	1.63
Consensus Log Po/w :	1.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.07
Solubility :	1.6 mg/ml ; 0.00842 mol/l
Class :	Soluble
Log S (Ali) :	-1.73
Solubility :	3.54 mg/ml ; 0.0186 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.35
Solubility :	0.0861 mg/ml ; 0.000452 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.26

Safety of [ 7205-98-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7205-98-3 ]

* 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 [ 7205-98-3 ]
Downstream synthetic route of [ 7205-98-3 ]

[ 7205-98-3 ] Synthesis Path-Upstream 1~20

1
[ 88-72-2 ]
[ 7205-98-3 ]
[ 16968-19-7 ]
[ 89303-33-3 ]

Reference： [1] Tetrahedron, 1984, vol. 40, # 10, p. 1863 - 1868

2
[ 7205-91-6 ]
[ 7205-98-3 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 10, p. 2955 - 2959
[2] Tetrahedron Letters, 1998, vol. 39, # 39, p. 7055 - 7058
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 5184
[4] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 6, p. 1225 - 1231[5] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 6, p. 1375 - 1382
[6] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 6829 - 6833
[7] Journal of Organic Chemistry, 1994, vol. 59, # 10, p. 2762 - 2765

3
[ 7205-94-9 ]
[ 7205-98-3 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 10, p. 2762 - 2765
[2] Istanbul Universitesi Fen Fakultesi Mecmuasi, 1957, vol. <C> 22, p. 383,387

4
[ 100-68-5 ]
[ 3112-85-4 ]
[ 7205-98-3 ]

Yield	Reaction Conditions	Operation in experiment
87 %Chromat.	With sodium hypochlorite pentahydrate In water; acetonitrile at 23 - 28℃; for 4 h;	General procedure: 0.25 g (2 mmol) of thioanisole as a substrate, 10 mL of acetonitrile and 2 mL of water were placed in a 50 mL three-necked flask.The internal temperature of the flask was 23 ° C.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added thereto at a time and stirred.The internal temperature of the flask rose to 28 ° C. and gradually decreased.GC analysis was carried out 3 hours after the start of the reaction, and 22percent of methyl phenyl sulfoxide,65percent of methyl phenyl sulfone was formed.As a by-product,6percent of chloromethyl phenyl sulfoxide,7percent of chloromethyl phenyl sulfone,A total of 0.8percent of higher order chlorides were observed.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added and stirring was continued for 1 hour.Thioanisole,Methyl phenyl sulfoxide was completely disappeared and 87percent of methyl phenyl sulfone was formed.As impurities,11percent chloromethyl phenyl sulfone,0.5percent dichloromethyl phenyl sulfone,Production of trichloromethyl phenyl sulfone 1.3percent was observed.

Reference： [1] Patent: JP2017/52730, 2017, A, . Location in patent: Paragraph 0046

5
[ 100-68-5 ]
[ 7205-94-9 ]
[ 1193-82-4 ]
[ 3112-85-4 ]
[ 7205-98-3 ]

Yield	Reaction Conditions	Operation in experiment
65 %Chromat.	With sodium hypochlorite pentahydrate In water; acetonitrile at 23 - 28℃; for 3 h;	General procedure: 0.25 g (2 mmol) of thioanisole as a substrate, 10 mL of acetonitrile and 2 mL of water were placed in a 50 mL three-necked flask.The internal temperature of the flask was 23 ° C.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added thereto at a time and stirred.The internal temperature of the flask rose to 28 ° C. and gradually decreased.GC analysis was carried out 3 hours after the start of the reaction, and 22percent of methyl phenyl sulfoxide,65percent of methyl phenyl sulfone was formed.As a by-product,6percent of chloromethyl phenyl sulfoxide,7percent of chloromethyl phenyl sulfone,A total of 0.8percent of higher order chlorides were observed.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added and stirring was continued for 1 hour.Thioanisole,Methyl phenyl sulfoxide was completely disappeared and 87percent of methyl phenyl sulfone was formed.As impurities,11percent chloromethyl phenyl sulfone,0.5percent dichloromethyl phenyl sulfone,Production of trichloromethyl phenyl sulfone 1.3percent was observed.

Reference： [1] Patent: JP2017/52730, 2017, A, . Location in patent: Paragraph 0046

6
[ 74-97-5 ]
[ 873-55-2 ]
[ 7205-98-3 ]

Reference： [1] Synthetic Communications, 2006, vol. 36, # 23, p. 3639 - 3646
[2] European Journal of Medicinal Chemistry, 2009, vol. 44, # 2, p. 653 - 659
[3] Journal of Organic Chemistry, 1984, vol. 49, # 9, p. 1488 - 1494
[4] Synthesis, 1987, # 1, p. 56 - 59

7
[ 7205-94-9 ]
[ 7205-98-3 ]
[ 140243-94-3 ]

Reference： [1] Chemistry Letters, 1995, # 7, p. 581 - 582
[2] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708

8
[ 195371-23-4 ]
[ 7205-98-3 ]

Reference： [1] Tetrahedron Letters, 1997, vol. 38, # 32, p. 5651 - 5654

9
[ 38009-92-6 ]
[ 7205-98-3 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 5, p. 877 - 881

10
[ 565446-69-7 ]
[ 7205-98-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 7, p. 1197 - 1205

11
[ 3406-03-9 ]
[ 7205-98-3 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 5, p. 877 - 881

12
[ 100-68-5 ]
[ 7205-98-3 ]

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 9, p. 3189 - 3192
[2] Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 54,64

13
[ 31540-74-6 ]
[ 7205-98-3 ]

Reference： [1] Chemische Berichte, 1888, vol. 21, p. 659

14
[ 108-98-5 ]
[ 7205-98-3 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 54,64

15
[ 2311-91-3 ]
[ 7205-91-6 ]
[ 7205-98-3 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 54,64

16
[ 3112-85-4 ]
[ 599-94-0 ]
[ 7205-98-3 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1987, # 3, p. 493 - 497

17
[ 75-09-2 ]
[ 873-55-2 ]
[ 7205-98-3 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2>40, p. 527

18
[ 64-17-5 ]
[ 75-09-2 ]
[ 873-55-2 ]
[ 7205-98-3 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2>40, p. 527

19
[ 7647-01-0 ]
[ 67-56-1 ]
[ 7205-98-3 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1954, vol. 587, p. 51,58

20
[ 64-17-5 ]
[ 31540-74-6 ]
[ 141-52-6 ]
[ 7205-98-3 ]
[ 98-11-3 ]

Reference： [1] Chemische Berichte, 1888, vol. 21, p. 659

[ 7205-98-3 ] Synthesis Path-Downstream 1~88

1
[ 7205-91-6 ]
[ 7205-98-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 2955 - 2959
[2]Tetrahedron Letters,1998,vol. 39,p. 7055 - 7058
[3]Journal of the American Chemical Society,1951,vol. 73,p. 5184
[4]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1982,vol. 31,p. 1225 - 1231
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1982,p. 1375 - 1382
[5]Journal of Organic Chemistry,2006,vol. 71,p. 6829 - 6833
[6]Journal of Organic Chemistry,1994,vol. 59,p. 2762 - 2765

2
[ 7205-94-9 ]
[ 7205-98-3 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2762 - 2765
[2]Istanbul Universitesi Fen Fakultesi Mecmuasi,1957,vol. <C> 22,p. 383,387

3
[ 7205-98-3 ]
[ 108-94-1 ]
[ 70150-86-6 ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 5500 - 5515
[2]Canadian Journal of Chemistry,1979,vol. 57,p. 258 - 266

4
[ 7205-98-3 ]
[ 100-52-7 ]
[ 40230-56-6 ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 5500 - 5515
[2]Canadian Journal of Chemistry,1979,vol. 57,p. 258 - 266
[3]Justus Liebigs Annalen der Chemie,1972,vol. 766,p. 89 - 97

5
[ 254-60-4 ]
[ 7205-98-3 ]
[ 87505-13-3 ]

Reference： [1]Tetrahedron Letters,1983,vol. <31> 24,p. 3279 - 3280
[2]Chemische Berichte,1991,vol. 124,p. 577 - 585

6
[ 253-72-5 ]
[ 7205-98-3 ]
[ 87505-11-1 ]

Reference： [1]Tetrahedron Letters,1983,vol. <31> 24,p. 3279 - 3280
[2]Chemische Berichte,1991,vol. 124,p. 577 - 585

7
[ 99-65-0 ]
[ 7205-98-3 ]
[ 89303-44-6 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 1863 - 1868
[2]Journal of Organic Chemistry,1984,vol. 49,p. 1488 - 1494

8
[ 1122-61-8 ]
[ 7205-98-3 ]
[ 88912-63-4 ]

Reference： [1]Liebigs Annalen der Chemie,1984,p. 8 - 14

9
[ 609-40-5 ]
[ 7205-98-3 ]
[ 93418-92-9 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1984,vol. 32,p. 69 - 74
[2]Tetrahedron,1995,vol. 51,p. 8339 - 8354
[3]Chemistry - A European Journal,2008,vol. 14,p. 6108 - 6118

10
[ 18368-61-1 ]
[ 7205-98-3 ]
[ 88912-70-3 ]
[ 88912-69-0 ]

Reference： [1]Liebigs Annalen der Chemie,1984,p. 8 - 14

11
[ 13508-96-8 ]
[ 7205-98-3 ]
[ 88912-66-7 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 5013 - 5030
[2]Liebigs Annalen der Chemie,1984,p. 8 - 14

12
[ 497-38-1 ]
[ 7205-98-3 ]
[ 89211-06-3 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1378 - 1382

13
[ 3034-42-2 ]
[ 7205-98-3 ]
[ 116248-38-5 ]
[ 116248-39-6 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1987,vol. 35,p. 287 - 292
[2]Chemistry - A European Journal,2008,vol. 14,p. 6108 - 6118

14
[ 1124-33-0 ]
[ 7205-98-3 ]
[ 88912-78-1 ]

Yield	Reaction Conditions	Operation in experiment
74%		Adapting the procedure of Makosza, et al, Liebigs Ann. Chem., 1984, 8-14, a stirred mixture of 4-nitro-pyridine-N-oxide (1.40 g, 10.0 [MMOL)] and [CHLOROMETHYLPHENYLSULFONE] (1.92 [G,] 10.0 [MMOL)] in DMSO (25 mL) in a cold water bath is treated with a solution of [KOH] (4.0 g, 71 mmol) in DMSO, stirred for 45 min, poured into 1.0 M hydrochloric acid and water and extracted with CH2CI2. The aqueous phase is filtered and the filtercake is dried in vacuo to afford the title compound, 1.20 [G] [(41 % YIELD).] The organic extracts are combined, dried over [MGSO4 AND CONCENTRATED IN VACUO.] The resultant wet solid is heated in boiling ethanol : water (4: 1) and filtered. The filtrate is cooled, concentrated and filtered. This [FILTERCAKE] is dried in vacuo to afford an additional portion of the title compound, 0.967 [G] (74% total yield), mp [219-220C,] identified by mass spectral and HNMR analyses.
	With potassium hydroxide; In ethanol; water; dimethyl sulfoxide;	EXAMPLE 69 Preparation of 4-Nitro-3-[(phenylsulfonyl)methyl]-pyridine-N-oxide Adapting the procedure of Makosza, et al, Liebigs Ann. Chem., 1984, 8-14, a stirred mixture of 4-nitro-pyridine-N-oxide (1.40 g, 10.0 mmol) and chloromethylphenylsulfone (1.92 g, 10.0 mmol) in DMSO (25 mL) in a cold water bath is treated with a solution of KOH (4.0 g, 71 mmol) in DMSO, stirred for 45 min, poured into 1.0 M hydrochloric acid and water and extracted with CH2Cl2. The aqueous phase is filtered and the filtercake is dried in vacuo to afford the title compound, 1.20 g (41% yield). The organic extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant wet solid is heated in boiling ethanol:water (4:1) and filtered. The filtrate is cooled, concentrated and filtered. This filtercake is dried in vacuo to afford an additional portion of the title compound, 0.967 g (74% total yield), mp 219-220 C., identified by mass spectral and H-NMR analyses.

Reference： [1]Patent: WO2003/101990,2003,A1 .Location in patent: Page 41
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6935 - 6938
[3]Liebigs Annalen der Chemie,1984,p. 8 - 14
[4]Liebigs Annalen der Chemie,1984,p. 8 - 14
[5]Patent: US2003/236278,2003,A1

15
[ 51-28-5 ]
[ 7205-98-3 ]
[ 92241-27-5 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4562 - 4563

16
[ 551-92-8 ]
[ 7205-98-3 ]
[ 116248-42-1 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1987,vol. 35,p. 287 - 292
[2]Synthetic Communications,2006,vol. 36,p. 3639 - 3646
[3]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

17
[ 607-34-1 ]
[ 7205-98-3 ]
[ 105199-19-7 ]

Reference： [1]Liebigs Annalen der Chemie,1986,p. 69 - 77

18
[ 3754-63-0 ]
[ 7205-98-3 ]
[ 89211-11-0 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1378 - 1382

19
[ 4812-45-7 ]
[ 7205-98-3 ]
7-Benzenesulfonylmethyl-3-chloro-5-nitro-1H-indazole [ No CAS ]

Reference： [1]Pharmazie,1988,vol. 43,p. 611 - 613

20
[ 50593-68-5 ]
[ 7205-98-3 ]
[ 119872-45-6 ]

Reference： [1]Pharmazie,1988,vol. 43,p. 611 - 613

21
[ 5327-44-6 ]
[ 7205-98-3 ]
[ 92241-35-5 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4562 - 4563

22
[ 6952-67-6 ]
[ 7205-98-3 ]
[ 89303-50-4 ]
[ 89303-40-2 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 1300 - 1306
[2]Journal of Organic Chemistry,1984,vol. 49,p. 1488 - 1494
[3]Tetrahedron,1984,vol. 40,p. 1863 - 1868

23
[ 100-17-4 ]
[ 7205-98-3 ]
[ 69709-39-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium tert-butylate; In tetrahydrofuran; at -60 - -20℃; for 1h;	EXAMPLE 16 Preparation of 4-Methoxy-1-nitro-2-[(phenylsulfonyl)methyl]benzene A solution of 4-nitroanisole (3.83 g, 25.0 mmol) and chloromethyl-phenylsulfone (4.76 g, 25.0 mmol) in dry THF is cooled to -60 C., treated with 1.0M KOt-Bu in THF (55.0 ML, 55.0 mmol), allowed to warm to -20 C. over 1 h, treated with glacial acetic acid, warmed to 20 C., treated with water and extracted with CH2Cl2.The combined extracts are dried over MgSO4 and concentrated in vacuo.The resulting solid is triturated with 25:75 ethyl acetate:hexanes and filtered.The filtercake is dried in vacuo to give the title product as a light tan solid, 7.05 g (92% yield), mp 167-169 C., characterized by mass spectral and HNMR analyses.

Reference： [1]Patent: US2003/232828,2003,A1 .Location in patent: Page 12
[2]Journal of Organic Chemistry,1984,vol. 49,p. 1488 - 1494
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5499 - 5502

24
[ 88-72-2 ]
[ 7205-98-3 ]
[ 16968-19-7 ]
[ 89303-33-3 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 1863 - 1868

25
[ 2403-53-4 ]
[ 7205-98-3 ]
[ 89303-15-1 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1488 - 1494

26
[ 121-18-6 ]
[ 7205-98-3 ]
[ 127204-94-8 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1989,vol. 37,p. 127 - 131

27
[ 7205-98-3 ]
[ 603-11-2 ]
[ 104825-38-9 ]
[ 104825-39-0 ]

Reference： [1]Synthesis,1986,p. 50 - 52

28
[ 7205-98-3 ]
[ 1091-94-7 ]
[ 89211-10-9 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1378 - 1382

29
[ 7205-98-3 ]
[ 384-22-5 ]
[ 89303-28-6 ]
[ 89303-34-4 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1488 - 1494
[2]Tetrahedron,1984,vol. 40,p. 1863 - 1868

30
[ 7205-98-3 ]
[ 384-22-5 ]
[ 89303-34-4 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 1863 - 1868

31
[ 7205-98-3 ]
[ 1167-52-8 ]
[ 89211-08-5 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1378 - 1382

32
[ 7205-98-3 ]
[ 1167-53-9 ]
[ 89211-09-6 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1378 - 1382

33
[ 7205-98-3 ]
[ 566-88-1 ]
[ 89211-07-4 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1378 - 1382

34
[ 7205-98-3 ]
[ 100-52-7 ]
[ 61937-46-0 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1982,vol. 31,p. 1225 - 1231
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1982,p. 1375 - 1382
[2]Journal of the American Chemical Society,1997,vol. 119,p. 981 - 986

35
[ 7205-98-3 ]
[ 98-95-3 ]
[ 69709-34-8 ]

Yield	Reaction Conditions	Operation in experiment
81%		[0179] A solution of nitrobenzene (3.08 g, 25.0 mmol) and chloromethylphenylsulfone (4.76 g, 25.0 mmol) in dry THF is cooled to -50 C. and treated with 1.0M KOtBu/THF (55.0 mL, 55.0 mmol). The reaction is allowed to warm to -30 C. over 1 h, treated with glacial acetic acid (3.6 mL), warmed to 20 C., treated with water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo. Chromatography (1:1 ethyl acetate:hexanes) of the resultant residue give the title product as a white solid, 5.62 g, (81% yield), mp 106-108 C., identified by mass spectral and HNMR analyses.

Reference： [1]Patent: US2004/24023,2004,A1 .Location in patent: Page 11-12
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1657 - 1660
[3]Tetrahedron,1984,vol. 40,p. 1863 - 1868
[4]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5499 - 5502

36
[ 7205-98-3 ]
[ 1569-16-0 ]
[ 129919-41-1 ]
[ 129919-40-0 ]

Reference： [1]Chemische Berichte,1991,vol. 124,p. 577 - 585

37
[ 7205-98-3 ]
[ 350-46-9 ]
[ 89303-18-4 ]

Yield	Reaction Conditions	Operation in experiment
62.8%		Step 1 2-Benzenesulfonylmethyl-4-fluoro-1-nitro-benzene To a solution of chloromethylphenyl sulfone (10.51 g, 55.13 mmol) in THF (110 mL) was added 5.9 mL (56 mmol) of 1-fluoro-4-nitrobenzene. The reaction mixture was chilled to 0 C., and 1.0 M potassium tert-butoxide in THF (145 mL, 145 mmol) was added dropwise. The reaction mixture was stirred under nitrogen at ambient temperature for one hour. Acetic acid (9 mL, 160 mmol) was then added. The reaction mixture was solvent evaporated and partitioned in brine and ethyl acetate. The organic phase was then dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was stirred in diethyl ether, filtered and dried in vacuo at 73 C. for 12 hours. 2-Benzenesulfonylmethyl-4-fluoro-1-nitrobenzene as a light brown-yellow solid was obtained (10.24 g, 62.8%): MP: 169-171 C.; Mass spectrum (-El, [M-H]-) m/z 294. 1HNMR (500 MHz, DMSO-d6): delta8.10-8.14 (m, 1H), 7.70-7.75 (m, 1H), 7.56-7.63 (m, 4H), 7.45-7.50 (m, 1H), 7.20 (dd, 1H, J=9.27 Hz and 2.81 Hz), 5.12 ppm (s, 2H). Elemental Analysis for C13H10FNO4S: Calcd: C, 52.88; H, 3.41; N, 4.74; Found: C, 52.63; H, 3.14; N, 4.66;

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 11113 - 11122
[2]Tetrahedron,1984,vol. 40,p. 1863 - 1868
[3]Patent: US2007/37802,2007,A1 .Location in patent: Page/Page column 16
[4]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5499 - 5502

38
[ 7205-98-3 ]
[ 586-78-7 ]
[ 69709-38-2 ]

Yield	Reaction Conditions	Operation in experiment
72%		Step 1: Preparation of 5-bromo-2-nitrobenzyl phenyl sulfone:CICH2SO2PhTo a stirred solution of 1 -bromo-4-nitrobenzene (5.05 g, 25 mmol) and chloromethyl- phenylsulfone (4.76 g, 25 mmol) in dry THF (50 mL) at -65 0C under nitrogen is added 1.0M KO'Bu in THF (55 mL, 55 mmol). The deep purple reaction is allowed to warm to 00C over 1 .5 hours and then treated with glacial acetic acid (4 mL). The reaction is diluted with water (100 mL) and saturated aqueous NaHCO3 (100 mL), and then extracted with CH2CI2 (2 x 200 mL). The extracts are dried (MgSO4) and concentrated in vacuo to a light orange solid. Trituration with ethyl acetate and hexanes affords the title compound as a pale yellow solid (6.45 g, 72%). Mp: 143 - 1440C. MS (ES-): 354 (M-H).
72%		Step 1 5-Bromo-2-nitrobenzyl phenyl sulfone To a stirred solution of 1-bromo-4-nitrobenzene (5.05 g, 25 mmol) and chloromethylphenylsulfone (4.76 g, 25 mmol) in dry THF (50 mL) at -65 C. under nitrogen is added 1.0M KOtBu in THF (55 mL, 55 mmol). The deep purple reaction is allowed to warm to 0 C. over 1.5 h and then treated with glacial acetic acid (4 mL). The reaction is diluted with water (100 mL) and saturated aqueous NaHCO3 (100 mL), and then extracted with CH2Cl2 (2×200 mL). The extracts are dried (MgSO4) and concentrated in vacuo to a light orange solid. Trituration with ethyl acetate and hexanes affords the title compound as a pale yellow solid (6.45 g, 72%). Mp: 143-144 C. MS (ES-): 354 (M-H)+

Reference： [1]Patent: WO2007/84841,2007,A2 .Location in patent: Page/Page column 69
[2]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7802 - 7815
[3]Patent: US2007/37802,2007,A1 .Location in patent: Page/Page column 87
[4]Journal of Organic Chemistry,1984,vol. 49,p. 1488 - 1494

39
[ 7205-98-3 ]
[ 2942-42-9 ]
[ 119872-46-7 ]

Reference： [1]Pharmazie,1988,vol. 43,p. 611 - 613

40
[ 7205-98-3 ]
[ 24108-33-6 ]
[ 114468-09-6 ]

Reference： [1]Liebigs Annalen der Chemie,1988,p. 627 - 632

41
[ 7205-98-3 ]
[ 28735-21-9 ]
[ 87505-20-2 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3277 - 3278
[2]Liebigs Annalen der Chemie,1988,p. 627 - 632

42
[ 7205-98-3 ]
[ 610-17-3 ]
[ 89303-24-2 ]
[ 89303-30-0 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1488 - 1494
[2]Tetrahedron,1984,vol. 40,p. 1863 - 1868

43
[ 7205-98-3 ]
[ 610-17-3 ]
[ 89303-30-0 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 1863 - 1868

44
[ 13195-50-1 ]
[ 7205-98-3 ]
(5-bromo-2-nitro-3-thienyl)methyl phenyl sulfone [ No CAS ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 8339 - 8354

45
[ 16689-02-4 ]
[ 7205-98-3 ]
(5-cyano-2-nitro-3-thienyl)methyl phenyl sulfone [ No CAS ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 8339 - 8354

46
[ 613-51-4 ]
[ 7205-98-3 ]
7-Nitro-8-<(phenylsulfonyl)methyl>quinoline [ No CAS ]

Reference： [1]Liebigs Annales,1996,p. 641 - 644

47
[ 7205-98-3 ]
{2-[(trimethylsilyl)methyl]prop-2-enyl}triphenylstannane [ No CAS ]
(4-Benzenesulfonyl-2-methylene-butyl)-trimethyl-silane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7028 - 7032

48
[ 5446-92-4 ]
[ 7205-98-3 ]
[ 115663-39-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	In tetrahydrofuran; acetic acid;	EXAMPLE 72 Preparation of 6-Methoxy-3-nitro-2-[(phenylsulfonyl)methyl]-pyridine A 1M KOt-Bu solution in tetrahydrofuran (50 mL, 50 mmol) is cooled to -40 C., treated portion-wise with a solution of chloromethyl phenyl sulfone (4.39 g, 23.0 mmol) and then with a solution of <strong>[5446-92-4]2-methoxy-5-nitropyridine</strong> (3.55 g, 23.0 mmol) in tetrahydrofuran, stirred for 45 min at -40 C., treated with glacial acetic acid (3.0 g, 50 mmol) and filtered. The filtercake is air-dried to give the title compound as a tan solid, 5.70 g (80% yield), mp 147-149 C., identified by mass spectral and H-NMR analyses.
80%		A 1 M KOt-Bu solution in tetrahydrofuran (50 mL, 50 [MMOL)] is cooled to [- 40C,] treated portion-wise with a solution of [CHLOROMETHYL] phenyl sulfone (4.39 g, 23.0 mmol) and then with a solution of <strong>[5446-92-4]2-methoxy-5-nitropyridine</strong> (3.55 g, 23.0 [MMOL)] in tetrahydrofuran, stirred for 45 min [AT-40C,] treated with glacial acetic acid (3.0 g, 50 [MMOL)] and filtered. The filtercake is air-dried to give the title compound as a tan solid, 5.70 g (80% yield), mp [147-149C,] identified by mass spectral and HNMR analyses.

Reference： [1]Polish Journal of Chemistry,1998,vol. 72,p. 1168 - 1172
[2]Patent: US2003/236278,2003,A1
[3]Patent: WO2003/101990,2003,A1 .Location in patent: Page 43
[4]Chemistry - A European Journal,2008,vol. 14,p. 6108 - 6118
[5]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6935 - 6938

49
[ 20265-37-6 ]
[ 7205-98-3 ]
5-Benzenesulfonylmethyl-3-methoxy-2-nitro-pyridine [ No CAS ]

Reference： [1]Polish Journal of Chemistry,1998,vol. 72,p. 1168 - 1172

50
[ 7205-98-3 ]
[ 31872-62-5 ]
2-Benzenesulfonylmethyl-4-methoxy-3-nitro-pyridine [ No CAS ]

Reference： [1]Polish Journal of Chemistry,1998,vol. 72,p. 1168 - 1172

51
[ 3034-42-2 ]
[ 7205-98-3 ]
[ 116248-38-5 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 4127 - 4129
[2]Synthetic Communications,2006,vol. 36,p. 3639 - 3646
[3]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

52
[ 7205-98-3 ]
[ 104651-47-0 ]
[(1R,3aR,4S,7aR)-1-((Z)-(S)-3-Benzenesulfonyl-1-methyl-allyl)-7a-methyl-octahydro-inden-4-yloxy]-tert-butyl-dimethyl-silane [ No CAS ]
[ 883104-65-2 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 1249 - 1251

53
[ 7205-98-3 ]
[ 3366-95-8 ]
1-[2-methyl-5-nitro-4-(phenylsulfonyl)methyl-1H-imidazol-1-yl]propan-2-ol [ No CAS ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3639 - 3646
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

54
[ 939-97-9 ]
[ 7205-98-3 ]
(2R,3R)-2-Benzenesulfonyl-3-(4-tert-butyl-phenyl)-oxirane [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8099 - 8103

55
[ 4548-45-2 ]
[ 7205-98-3 ]
[ 744198-04-7 ]
[ 88912-74-7 ]

Yield	Reaction Conditions	Operation in experiment
23%; 10%	With potassium tert-butylate; In tetrahydrofuran; at -65 - 0℃; for 1.5h;	[0141] A stirred solution of 2-chloro-5-nitro-pyridine (3.97 g, 25.0 mmol) and chloromethylphenylsulfone (4.76 g, 25.0 mmol) in dry THF at ?65 C. under nitrogen is treated with 1.0M KO-t-Bu in THF (55.0 mL, 55.0 mmol), allowed to warm to 0 C. over 1.5 h, treated with glacial acetic acid (5.5 mL), stirred for 0.5 h, treated with saturated aqueous NaHCO3, stirred for 2 h, and extracted with CH2Cl2. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford a brown oil. The oil is chromatographed (silica gel, 50:50 EtOAc:hexanes as eluent) to give a slightly yellow solid identified by NMR as a mixture of the two title regioisomers A and B (5.67 g, 73%). A second chromatography (silica gel, 40:60 EtOAc:hexanes as eluent) provides the title compound A as a white solid, 1.75 g (23% yield), identified by NMR and mass spectral analyses and the title compound B as a white solid, 0.79 g (10% yield), identified by NMR and mass spectral analyses.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6935 - 6938
[2]Patent: US2004/167030,2004,A1 .Location in patent: Page 10

56
[ 7205-98-3 ]
[ 55403-34-4 ]
[ 744198-01-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium tert-butylate; In tetrahydrofuran; at -60 - -10℃; for 1h;	[0135] A stirred solution of 1-methyl-4-(5-nitropyridin-2-yl)piperazine (1.10 g, 5.00 mmol) and chloromethylphenylsulfone (0.950 g, 5.00 mmol) in dry THF, under nitrogen, is cooled to ?60 C., treated with 1.0 M KOtBu in THF (10.0 mL, 10.0 mmol), allowed to warm to ?10 C. over a 1 h period, quenched with acetic acid, treated sequentially with water and saturated aqueous NaHCO3 and extracted with CH2Cl2. The combined extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from EtOAc to give the title compound as a yellow solid, 1.60 g (85% yield), mp: 170-172 C., identified by mass spectral and NMR analyses.

Reference： [1]Patent: US2004/167030,2004,A1 .Location in patent: Page 9

57
[ 7205-98-3 ]
[ 16155-08-1 ]
[ 744218-37-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium tert-butylate; In tetrahydrofuran; at -60 - -20℃; for 1h;	EXAMPLE 2 Preparation of 1-Benzyl-4-{4-nitro-3-[(phenylsulfonyl)methyl]phenyl}piperazine A stirred solution of 1-benzyl-4-(4-nitrophenyl)piperazine (5.95 g, 20.0 mmol) and chloromethylphenylsulfone (3.82 g, 20.0 mmol) in dry THF under nitrogen at -60 C. is treated with 1.0M KO-t-Bu in THF (44.0 ML, 44.0 mmol), warmed to -20 C. over a 1 h period, quenched with acetic acid and treated sequentially with water, saturated aqueous NaHCO3 and ether.The phases are separated and the aqueous phase is extracted with ether.The combined ethers are washed with water and brine, dried over MgSO4 and concentrated in vacuo.The resultant residue is chromatographed (silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent) to give the title compound as a yellow solid, 7.52 g (83% yield), mp 145-146 C., characterized by NMR and mass spectral analyses.

Reference： [1]Patent: US2004/167122,2004,A1 .Location in patent: Page/Page column 12-13

58
[ 577-19-5 ]
[ 7205-98-3 ]
[ 689772-86-9 ]

Yield	Reaction Conditions	Operation in experiment
73%		Step 1 3-Bromo-2-nitrobenzyl phenyl sulfone To a stirred solution of 1-bromo-2-nitrobenzene (10.1 g, 50 mmol) and chloromethylphenylsulfone (9.5 g, 50 mmol) in dry THF (100 mL) at -65 C. under nitrogen is added 1.0M KOtBu in THF (110 mL, 110 mmol). The deep purple reaction is allowed to warm to 0 C. over 1.5 hours and then treated with glacial acetic acid (8 mL). The reaction is diluted with water (200 mL) and saturated aqueous NaHCO3 (200 mL), and then extracted with CH2Cl2 (2×400 mL). The extracts are dried (MgSO4) and concentrated in vacuo to a light orange solid. Trituration with ethyl acetate and hexanes affords the title compound as a pale yellow solid (13 g, 73%). Mp: 138-141 C. MS (ES-): 354 (M-H)

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7802 - 7815
[2]Patent: US2007/37802,2007,A1 .Location in patent: Page/Page column 83

59
[ 925450-47-1 ]
[ 7205-98-3 ]
[ 925450-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; at -78 - 40℃; for 5.5h;	Step 1) 1-Benzenesulfonylmethyl-3-(2-chloro-ethoxy)-5-fluoro-2-nitro-benzene A mixture of 2-(2-chloroethoxy)-4-fluoro-1-nitrobenzene (1.3 g, 6 mmoles) and 1-chloromethane-sulfonyl-benzene (1.7 g, 9 mmoles) was stirred in THF (50 mL) at -78 C., in a round bottom flask under nitrogen. A solution of 1M potassium t-butoxide was added dropwise (18 mL, 18 mmoles) over a half hour period. Temperature was allowed to rise to 40 C., and the reaction mixture was stirred at this temperature for 5 hours. The reaction mixture was poured into cold 2N HCl, extracted with EtOAc, dried over Na2SO4, and concentrated under vacuum. Compound was recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid (1.98 g, 5.3 mmoles).

Reference： [1]Patent: US2007/37802,2007,A1 .Location in patent: Page/Page column 71

60
[ 7205-98-3 ]
[ 455-93-6 ]
[ 1101862-59-2 ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 2048 - 2053
[2]Russian Chemical Bulletin,2009,vol. 58,p. 170 - 175

61
[ 609-40-5 ]
[ 86-57-7 ]
[ 7205-98-3 ]
[ 1050589-63-3 ]
[ 93418-92-9 ]