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66176-39-4 Usage

Chemical Properties

off-white to light yellow crystalline powder

Uses

4-(Bromomethyl)benzenesulfonyl chloride may be used to synthesize:4-bromomethyl-N-(6-methoxy-quinolin-8-yl)-benzenesulfonamidebenzene-sulfonamide derivatives, which are potent Chemokine Receptor Type 4 (CXCR4) inhibitorsimidazole derivatives having antifungal activity

Check Digit Verification of cas no

The CAS Registry Mumber 66176-39-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,1,7 and 6 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 66176-39:
(7*6)+(6*6)+(5*1)+(4*7)+(3*6)+(2*3)+(1*9)=144
144 % 10 = 4
So 66176-39-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H6BrClO2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,5H2

66176-39-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (B3936)  4-(Bromomethyl)benzenesulfonyl Chloride  >95.0%(GC)(T)

  • 66176-39-4

  • 1g

  • 315.00CNY

  • Detail
  • TCI America

  • (B3936)  4-(Bromomethyl)benzenesulfonyl Chloride  >95.0%(GC)(T)

  • 66176-39-4

  • 5g

  • 1,100.00CNY

  • Detail
  • Alfa Aesar

  • (A10120)  4-(Bromomethyl)benzenesulfonyl chloride, 95%   

  • 66176-39-4

  • 1g

  • 231.0CNY

  • Detail
  • Alfa Aesar

  • (A10120)  4-(Bromomethyl)benzenesulfonyl chloride, 95%   

  • 66176-39-4

  • 5g

  • 986.0CNY

  • Detail
  • Alfa Aesar

  • (A10120)  4-(Bromomethyl)benzenesulfonyl chloride, 95%   

  • 66176-39-4

  • 25g

  • 4176.0CNY

  • Detail
  • Aldrich

  • (557153)  4-(Bromomethyl)benzenesulfonylchloride  95%

  • 66176-39-4

  • 557153-1G

  • 347.49CNY

  • Detail
  • Aldrich

  • (557153)  4-(Bromomethyl)benzenesulfonylchloride  95%

  • 66176-39-4

  • 557153-5G

  • 1,203.93CNY

  • Detail

66176-39-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(Bromomethyl)benzenesulfonyl chloride

1.2 Other means of identification

Product number -
Other names 4-(bromomethyl)benzenesulfonyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:66176-39-4 SDS

66176-39-4Synthetic route

α-bromo-p-toluidine
63516-03-0

α-bromo-p-toluidine

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

Conditions
ConditionsYield
Stage #1: α-bromo-p-toluidine With hydrogenchloride; sodium nitrite In water at -5 - 0℃;
Stage #2: With thionyl chloride; copper(l) chloride In water at -5 - 0℃;
75.9%
azobisisobutyronitrile
34241-39-9

azobisisobutyronitrile

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

A

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

B

4-(1-bromo-ethyl)-benzenesulfonyl chloride
25426-48-6

4-(1-bromo-ethyl)-benzenesulfonyl chloride

Conditions
ConditionsYield
With N-Bromosuccinimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; benzeneA n/a
B 66%
azobisisobutyronitrile
34241-39-9

azobisisobutyronitrile

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

Conditions
ConditionsYield
With N-Bromosuccinimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; benzene66%
With N-Bromosuccinimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; benzene66%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80℃; for 10h; Inert atmosphere;65%
With N-Bromosuccinimide; trityl tetrafluoroborate In dichloromethane at 20℃; Irradiation; Inert atmosphere; chemoselective reaction;55%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene for 23h; Reflux;36%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

phenylmethanethiol
100-53-8

phenylmethanethiol

A

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

B

4-(benzylmercapto)benzaldehyde
78832-95-8

4-(benzylmercapto)benzaldehyde

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

benzylamine
100-46-9

benzylamine

4-bromomethyl-benzenesulfonic acid benzylamide

4-bromomethyl-benzenesulfonic acid benzylamide

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
piperidine
110-89-4

piperidine

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

1-((4-(bromomethyl)phenyl)sulfonyl)piperidine

1-((4-(bromomethyl)phenyl)sulfonyl)piperidine

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
With triethylamine In dichloromethane at 0℃; for 1.25h; Inert atmosphere;
With sodium carbonate In water at 20℃; pH=9-10;
1-indoline
496-15-1

1-indoline

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

1-(4-bromomethyl-benzenesulfonyl)-2,3-dihydro-1H-indole

1-(4-bromomethyl-benzenesulfonyl)-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

1-(4-bromomethyl-benzenesulfonyl)-1H-benzotriazole

1-(4-bromomethyl-benzenesulfonyl)-1H-benzotriazole

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

diethylamine
109-89-7

diethylamine

4-(bromomethyl)-N,N-diethylbenzenesulfonamide
15148-73-9

4-(bromomethyl)-N,N-diethylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h;
With triethylamine In dichloromethane at 0℃; for 1.25h; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃; for 1h;0.10 g
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-benzyl-4-(bromomethyl)-N-methylbenzenesulfonamide
125734-38-5

N-benzyl-4-(bromomethyl)-N-methylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
In dichloromethane at 20℃;20%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-bromomethyl-benzenesulfonamide
40724-47-8

4-bromomethyl-benzenesulfonamide

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran; water at 20℃; for 1h;98%
With ammonia In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;96.8%
With ammonia In dichloromethane at 0℃; for 0.166667h;96.8%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

8-amino-6-methoxy-quinoline hydrobromide
106492-78-8

8-amino-6-methoxy-quinoline hydrobromide

4-bromomethyl-N-(6-methoxy-quinolin-8-yl)-benzenesulfonamide
936028-23-8

4-bromomethyl-N-(6-methoxy-quinolin-8-yl)-benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane; acetone at 0℃; for 0.333333h;98%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

isopropylamine
75-31-0

isopropylamine

4-(bromomethyl)-N-(propan-2-yl)benzene-1-sulfonamide
448965-27-3

4-(bromomethyl)-N-(propan-2-yl)benzene-1-sulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h;97%
In tetrahydrofuran at -78℃;49%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

N-methyl-2-pyridinemethanamine
21035-59-6

N-methyl-2-pyridinemethanamine

4-(bromomethyl)-N-methyl-N-(pyridin-2-ylmethyl)benzenesulfonamide
1431950-01-4

4-(bromomethyl)-N-methyl-N-(pyridin-2-ylmethyl)benzenesulfonamide

Conditions
ConditionsYield
In dichloromethane at 20℃;94%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-(bromomethyl)benzene-1-sulfonyl fluoride

4-(bromomethyl)benzene-1-sulfonyl fluoride

Conditions
ConditionsYield
With potassium hydrogen difluoride In acetonitrile at 20℃; for 2h;93%
With potassium hydrogen difluoride In water; acetonitrile at 20℃;82%
1-(2-hydroxyethyl)piperazine
103-76-4

1-(2-hydroxyethyl)piperazine

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

2-(4-((4-(bromomethyl)phenyl)sulfonyl)piperazin-1-yl)ethan-1-ol

2-(4-((4-(bromomethyl)phenyl)sulfonyl)piperazin-1-yl)ethan-1-ol

Conditions
ConditionsYield
In diethyl ether at -5℃; for 3h;93%
tri-n-butyl phosphite
102-85-2

tri-n-butyl phosphite

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

dibutyl (4-chlorosulfonylphenyl)methylphosphonate

dibutyl (4-chlorosulfonylphenyl)methylphosphonate

Conditions
ConditionsYield
at 160℃; for 12h;90%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

p-(bromomethyl)benzenosulfonylhydrazide
877931-61-8

p-(bromomethyl)benzenosulfonylhydrazide

Conditions
ConditionsYield
With hydrazine hydrate In tetrahydrofuran; water for 0.25h; cooling;90%
4-propylaniline
2696-84-6

4-propylaniline

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-(bromomethyl)-N-(4-propylphenyl)benzenesulfonamide
1308718-78-6

4-(bromomethyl)-N-(4-propylphenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 2h;90%
4-[2-(diethylamino)ethoxy]aniline
38519-63-0

4-[2-(diethylamino)ethoxy]aniline

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-(bromomethyl)-N-{4-[2-(diethylamino)ethoxy]phenyl}benzenesulfonamide
1431950-54-7

4-(bromomethyl)-N-{4-[2-(diethylamino)ethoxy]phenyl}benzenesulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 12h;90%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

N-(4-tert-butylbenzyl)methylamine
65542-26-9

N-(4-tert-butylbenzyl)methylamine

4-bromomethyl-N-4-tert-butylbenzyl-N-methylbenzenesulfonamide
1431950-14-9

4-bromomethyl-N-4-tert-butylbenzyl-N-methylbenzenesulfonamide

Conditions
ConditionsYield
In dichloromethane at 20℃;90%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

isobutylamine
78-81-9

isobutylamine

4-(bromomethyl)-N-(isobutyl)benzenesulfonamide
1308718-72-0

4-(bromomethyl)-N-(isobutyl)benzenesulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h;88%
With pyridine In dichloromethane at 20℃; for 1.5h;48%
With pyridine In dichloromethane at 20℃; for 1.5h;48%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

methyl 3-aminopropanoate hydrochloride
3196-73-4

methyl 3-aminopropanoate hydrochloride

C11H14BrNO4S

C11H14BrNO4S

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane for 18h;87%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

[(S)-1-(4-Bromomethyl-benzenesulfonyl)-pyrrolidin-2-yl]-diphenyl-methanol
910542-57-3

[(S)-1-(4-Bromomethyl-benzenesulfonyl)-pyrrolidin-2-yl]-diphenyl-methanol

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0℃; for 6h;86%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

L-leucine ethyl ester hydrochloride
2743-40-0

L-leucine ethyl ester hydrochloride

N-4-bromomethylphenylsulphonyl-L-leucine ethyl ester
141834-14-2

N-4-bromomethylphenylsulphonyl-L-leucine ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran85%
With triethylamine In tetrahydrofuran82%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

aniline
62-53-3

aniline

4-(bromomethyl)-N-(phenyl)benzenesulfonamide
1308718-76-4

4-(bromomethyl)-N-(phenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 2h;84%
In dichloromethane at 25℃; for 20h;
propylamine
107-10-8

propylamine

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-(bromomethyl)-N-(propyl)benzenesulfonamide
1308718-63-9

4-(bromomethyl)-N-(propyl)benzenesulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h;82%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

ethyl β-alaninate hydrochloride
4244-84-2

ethyl β-alaninate hydrochloride

ethyl 3-({[4-(bromomethyl)phenyl]sulfonyl}amino)propionate
307989-07-7

ethyl 3-({[4-(bromomethyl)phenyl]sulfonyl}amino)propionate

Conditions
ConditionsYield
Stage #1: 4-(bromomethyl)benzene-1-sulfonyl chloride; ethyl β-alaninate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: With hydrogenchloride In water; ethyl acetate
Stage #3: With sodium hydrogencarbonate In water; ethyl acetate
81%
4-Isopropylaniline
99-88-7

4-Isopropylaniline

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-(bromomethyl)-N-(4-isopropylphenyl)benzenesulfonamide
1308718-81-1

4-(bromomethyl)-N-(4-isopropylphenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 2h;81%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

2-((tert-butyldimethylsilyl)oxy)aniline
69589-21-5

2-((tert-butyldimethylsilyl)oxy)aniline

4-(bromomethyl)-N-(2-(tert-butyldimethylsilyloxy)phenyl)benzenesulfonamide
1455483-41-6

4-(bromomethyl)-N-(2-(tert-butyldimethylsilyloxy)phenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;81%
4-methoxy-N-methylbenzylamine
702-24-9

4-methoxy-N-methylbenzylamine

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-(bromomethyl)-N-(4-methoxybenzyl)-N-methylbenzenesulfonamide
1431950-16-1

4-(bromomethyl)-N-(4-methoxybenzyl)-N-methylbenzenesulfonamide

Conditions
ConditionsYield
In dichloromethane at 20℃;81%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

tert-Butyl [(1S,2S)-2-amino-1,2-diphenylethyl]carbamate

tert-Butyl [(1S,2S)-2-amino-1,2-diphenylethyl]carbamate

(S,S)-N-(tert-butyloxycarbonyl)-N'-(4-bromomethylphenylsulfonyl)-1,2-diphenylethylenediamine

(S,S)-N-(tert-butyloxycarbonyl)-N'-(4-bromomethylphenylsulfonyl)-1,2-diphenylethylenediamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;81%
With triethylamine In dichloromethane at 20℃; for 2h; Cooling with ice;
morpholine
110-91-8

morpholine

4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-((4-(bromomethyl)benzene)sulfonyl)morpholine
138385-04-3

4-((4-(bromomethyl)benzene)sulfonyl)morpholine

Conditions
ConditionsYield
Stage #1: morpholine With triethylamine In diethyl ether at 0℃; Inert atmosphere;
Stage #2: 4-(bromomethyl)benzene-1-sulfonyl chloride In diethyl ether at 20℃; for 6h; Inert atmosphere;
80%
With triethylamine In diethyl ether at 0 - 20℃; for 6h; Inert atmosphere;80%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h;70%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

4-(bromomethyl)benzenesulfonyl azide
1069135-16-5

4-(bromomethyl)benzenesulfonyl azide

Conditions
ConditionsYield
With sodium azide In water; acetone at 20℃; for 3h; Inert atmosphere;78%
With sodium azide In water; acetone at 20℃; for 3h;78%
With sodium azide In water; acetone at 20℃; for 12h;

66176-39-4Relevant articles and documents

Preparation method of substituted benzene sulfonyl chloride

-

Paragraph 0051-0054, (2021/05/08)

The invention provides a preparation method of substituted benzene sulfonyl chloride, which comprises the following steps: carrying out diazotization reaction on an aniline compound with a structure as shown in a formula I to obtain fluoboric acid diazonium salt with a structure as shown in a formula II; obtaining substituted benzene sulfonyl chloride with a structure as shown in a formula III from the fluoboric acid diazonium salt with the structure as shown in the formula II; wherein R is selected from any one of ortho-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, meta-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, para-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano and acetyl. The preparation method of the substituted benzene sulfonyl chloride provided by the invention is simple in reaction process, easy to operate, ideal in effect and suitable for industrial production.

Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.

Ni, Shengjun,El Remaily, Mahmoud Abd El Aleem Ali Ali,Franzén, Johan

supporting information, p. 4197 - 4204 (2018/09/25)

The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).

4-PHENYL-5-OXO-1,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES THE TREATMENT OF INFERTILITY

-

Page/Page column 53, (2010/11/24)

The present invention relates to 4-phenyl-5-oxo-l,4)5,6,7,8-hexahydroquinoline derivatives according to Formula I, Formula I or a pharmaceutically acceptable salt thereof, wherein R1 is (l-6C)alkyl, (2-6C)alkenyl or (2-6C)aDcynyl; R2, R3 are independently halogen, (l-4C)allcyl, (2-4C)alkenyl, (2-4C)- alkynyl, (1 -4C)aBcoxy, (3-4C)alkenyloxy or (3-4C)alkynyloxy; R4 is phenyl or (2-5C)- heteroaryl, both substituted with R7 and optionally substituted on the (hetero)aromatic ring with one or more substituents selected from hydroxy, amino, halogen, nitro, trifluoromethyl, cyano, (l-4C)alkyl, (l-4C)alkoxy , (l-4C)alkylthio and (di)(l-4C)- alkylamino. The invention also relates to pharmaceutical compositions comprising said derivatives, as well as to the use of these 4-phenyl-5-oxo-l, 4,5,6, 7,8-hexahydro- quinoline derivatives in therapy, more specifically for the treatment of infertility

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