[ CAS No. 2632-14-6 ] {[proInfo.proName]}

Name: 2632-14-6|2-Bromo-1-(4-ethylphenyl)ethanone|95%
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SKU: A210411
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Quality Control of [ 2632-14-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2632-14-6 ]

Product Details of [ 2632-14-6 ]

CAS No. :	2632-14-6	MDL No. :	MFCD00981997
Formula :	C₁₀H₁₁BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XNYSPDGJBPTDDI-UHFFFAOYSA-N
M.W :	227.10	Pubchem ID :	12401951
Synonyms :

Calculated chemistry of [ 2632-14-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.28
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.22
Log Po/w (XLOGP3) :	2.99
Log Po/w (WLOGP) :	2.83
Log Po/w (MLOGP) :	2.83
Log Po/w (SILICOS-IT) :	3.52
Consensus Log Po/w :	2.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.113 mg/ml ; 0.000497 mol/l
Class :	Soluble
Log S (Ali) :	-3.01
Solubility :	0.221 mg/ml ; 0.000972 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.4
Solubility :	0.009 mg/ml ; 0.0000396 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 2632-14-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2632-14-6 ]

* 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 [ 2632-14-6 ]
Downstream synthetic route of [ 2632-14-6 ]

[ 2632-14-6 ] Synthesis Path-Upstream 1~5

1
[ 937-30-4 ]
[ 2632-14-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With phenyltrimethylammonium tribromide In tetrahydrofuran at 0 - 20℃; for 1.33333 h;	Preparation of 2-bromo-1-(4-ethylphenyl)ethanone (Chem. Abstr. Reg. No. 2632- 14-6); 4'-ethylacetophenone (9 mL, 60 mmol) was dissolved in 100 mL anhydrous tetrahydrofuran, cooled to 0°C, then added phenyltrimethylammonium tribromide (22.6 g, 60 mmol) in portions. A precipitate slowly forms. The reaction mixture was stirred at 0⁰C for 1 hour, then at ambient temperature for 20 minutes. The concentrated reaction mixture was diluted with 200 mL diethyl ether, washed with water (3 x 150 mL), brine, and dried with magnesium sulfate, filtered. Thw filtrate was concentrated to yield the title compound. (15.9 g, quant.) MS: 227,229.03 (Br pattern); Anal. HPLC Retention time = 18.6 minutes (>99percent pure).
86%	With Oxone; ammonium bromide In methanol for 1.5 h; Reflux	General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH₄Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3.x.25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of ¹H NMR and mass spectral data.

Reference： [1] Patent: WO2008/84300, 2008, A1, . Location in patent: Page/Page column 35
[2] Heterocycles, 1992, vol. 34, # 4, p. 747 - 756
[3] Journal of Heterocyclic Chemistry, 2013, vol. 50, # SUPPL.1, p. E126-E130
[4] Synthetic Communications, 2013, vol. 43, # 19, p. 2603 - 2614
[5] RSC Advances, 2016, vol. 6, # 79, p. 75651 - 75663
[6] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
[7] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1746 - 1749
[8] Chinese Journal of Chemistry, 2012, vol. 30, # 6, p. 1339 - 1344
[9] Archiv der Pharmazie, 2014, vol. 347, # 2, p. 89 - 95
[10] Journal of the Chinese Chemical Society, 2017, vol. 64, # 12, p. 1408 - 1416

2
[ 937-30-4 ]
[ 2632-14-6 ]
[ 41036-98-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-Bromosuccinimide; silica gel In methanol for 0.266667 h; Reflux	General procedure: The α-bromination reaction was carried out using acetophenone (1200 mg, 10 mmol), N-bromosuccinimide (2136 mg, 12 mmol), 10percent (w/w) silica gel (120mg) in 10 mL of methanol at reflux conditions until the disappearance of the substrate. (Note: 2136mg of N-bromosuccinimide was added portion wise i.e. 356 mg for each time in six portions). The progress of the reaction was monitored by TLC. The reaction mass was filtered after the completion of the reaction as per TLC and the catalyst was collected for reuse. The filtrate was concentrated under vacuum. Double distilled water was added to the reaction mixture and quenched with aqueous sodium thiosulfate and the product extracted with dichloromethane (Caution: Severe burning sensation of eyes was observed during the work-up process). The layers were separated and the organic layer was collected and washed thrice with distilled water (3×50mL). The collected organic layer was dried over anhydrous Na₂SO₄, filtered and concentrated. The obtained crude product was purified by column chromatography over silica gel (60–120 mesh) using n-hexane–EtOAc (99:1 ratio). With the aim of studying the recycling of the catalyst, the isolated catalyst was washed with ethyl acetate (5mL) after its filtration from the reaction medium, collected and dried in vacuum at 70°C to a constant weight. Subsequently it was reused for the α-bromination of acetophenone and achieved 95percent, 86percent and 83percent yields of product (2a) for first, second and third reuse of catalyst respectively. All products gave spectroscopic data in agreement with the literature [15,21,27–30]. The method is also very practical for scale up in process development. We attempted large scale (100 gram scale) synthesis of 2-bromo-1-phenylethanone 2a and obtained fruitful results with isolated yields ranging from 93percent to 96percent.

Reference： [1] Chinese Chemical Letters, 2014, vol. 25, # 1, p. 179 - 182

3
[ 1345683-42-2 ]
[ 2632-14-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 40℃; for 6 h; Green chemistry	General procedure: A mixture of haloalkyne (0.5 mmol), AgF (5molpercent) and water (1 equiv.) in TFA (1 mL) was stirred at 40°C for 6h, after which TFA was distilled out for reuse. The residue was separated by column chromatography to give the pure sample.

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 7, p. 1373 - 1375

4
[ 40307-11-7 ]
[ 2632-14-6 ]

Reference： [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 4, p. 781 - 785

5
[ 100-41-4 ]
[ 598-21-0 ]
[ 2632-14-6 ]

Reference： [1] Journal of Biological Chemistry, 1915, vol. 21, p. 445

[ 2632-14-6 ] Synthesis Path-Downstream 1~88

1
[ 109-02-4 ]
[ 2632-14-6 ]
4-(4-ethyl-phenacyl)-4-methyl-morpholinium; bromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 4011

2
[ 2632-14-6 ]
[ 50690-09-0 ]
[ 333-20-0 ]
[ 6097-24-1 ]

Reference： [1]Journal Of Scientific and Industrial Research,1959,vol. 18 B,p. 392

3
[ 2632-14-6 ]
[ 484-51-5 ]
(4-ethyl-phenyl)-(4,8-dimethoxy-3-methyl-benzo[1,2-b;5,4-b']difuran-2-yl)-ketone [ No CAS ]

Reference： [1]Journal of the Chemical Society,1955,p. 3688,3692

4
[ 100-41-4 ]
[ 598-21-0 ]
[ 2632-14-6 ]

Reference： [1]Journal of Biological Chemistry,1915,vol. 21,p. 445

5
[ 2632-14-6 ]
[ 79-40-3 ]
[ 72997-73-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1979,vol. 321,p. 643 - 654

6
[ 2632-14-6 ]
[ 603-35-0 ]
[2-(4-Ethyl-phenyl)-2-oxo-ethyl]-triphenyl-phosphonium; bromide [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1972,vol. 37,p. 3950 - 3955

7
[ 616-47-7 ]
[ 2632-14-6 ]
[ 103793-25-5 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2301 - 2306

8
[ 3971-69-5 ]
[ 2632-14-6 ]
[ 78394-77-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 564 - 568
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 653 - 657

9
[ 31146-39-1 ]
[ 2632-14-6 ]
[ 78394-92-0 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 564 - 568
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 653 - 657

10
[ 937-30-4 ]
[ 2632-14-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 0 - 20℃; for 1.33333h;	Preparation of 2-bromo-1-(4-ethylphenyl)ethanone (Chem. Abstr. Reg. No. 2632- 14-6); 4'-ethylacetophenone (9 mL, 60 mmol) was dissolved in 100 mL anhydrous tetrahydrofuran, cooled to 0C, then added phenyltrimethylammonium tribromide (22.6 g, 60 mmol) in portions. A precipitate slowly forms. The reaction mixture was stirred at 00C for 1 hour, then at ambient temperature for 20 minutes. The concentrated reaction mixture was diluted with 200 mL diethyl ether, washed with water (3 x 150 mL), brine, and dried with magnesium sulfate, filtered. Thw filtrate was concentrated to yield the title compound. (15.9 g, quant.) MS: 227,229.03 (Br pattern); Anal. HPLC Retention time = 18.6 minutes (>99% pure).
93%	With N-Bromosuccinimide; toluene-4-sulfonic acid; In acetonitrile; for 2h;Reflux; Inert atmosphere;	To a solution of 1-(4-theylphenyl)-ethanone (6.00 g, 40.4 mmol) inacetonitrile (200 mL) was added p-toluenesulfonic acid (10.46 g,60.8 mmol) followed by N-bromosuccinimide (7.20 g, 40.4 mmol). Themixture was warmed to reflux under nitrogen and maintained for 2 h.The mixture was cooled to room temperature, concentrated in vacuo,dissolved in CH2Cl2 (250 mL), washed with water (2×250 mL) anddried (Na2SO4). Concentration in vacuo afforded the crude bromide as ayellow-brown oil which was purified by chromatography chromatographyon a column of silica gel using the flash technique (40mm OD,100 g, 230-400 mesh) eluted with CH2Cl2. Fractions containing the target bromide were combined and concentrated in vacuo to afford8.54 g (93%) of 2-bromo-1-(4-ethylphenyl)-ethanone as a pale yellowoil. 1H NMR (400 MHz, CDCl3): delta=7.90 (d, J=8.3 Hz, 2), 7.64 (d,J=8.3 Hz, 2), 4.48 (s, 2), 2.74 (q, J=7.6 Hz, 2), 1.27 (t, J=7.6 Hz,3).
86%	With Oxone; ammonium bromide; In methanol; for 1.5h;Reflux;	General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3×25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data.

With copper(ll) bromide; In ethyl acetate;Reflux; Sonication;

General procedure: 20 mmol of the appropriate acyl ketone was dissolved in 40 mL of ethyl acetate to make a 0.5 M solution. 2.6 equivalents of CuBr2 was added and the mixture refluxed with a condenser for 3-5 h until the starting ketone was fully consumed as indicated by TLC or 1H NMR. Once the reaction was complete, the mixture was cooled, and then the ethyl acetate was removed under reduced pressure. Hexanes were added to the crude solid and the mixture was sonicated for 5 min. The hexanes were decanted and a fresh volume was added to the remaining solids, again sonicating for 5min. This process was repeated once more, for a total of 3 extractions. The combined hexane layers, which typically appeared as an amber or light yellow solution, were evaporated under reduced pressure to yield the crude product which typically appeared as yellow or orange oil. If a sonicator is not available, a Soxhlet extraction with hexanes gives similar yields. The crude bromoketone oil was next dissolved in a 5:1 mixture of ethanol/water to give a 0.4 M solution overall. The solution was cooled over ice, and then 3 equivalents of NaCN were added. The reaction was stirred overnight (16 h), allowing the ice to melt. The solution was then diluted with enough water to roughly double the initial volume. This solution was filtered through a Celite pad to remove suspended solids. This solution was then acidified by adding concentrated HCl to a stirring solution. CAUTION This will cause the evolution of HCN gas Only perform in a well-ventilated fume hood The acidified solution was allowed to stir for 15 minutes. The solution was checked by pH paper to ensure that it was acidic (pH ? 2). If not, additional HCl was added, taking the same precautions noted above. Once the solution was acidic, it was transferred to a separatory funnel and extracted 3x with DCM. The organic layers were combined, dried over magnesium sulfate, filtered, and then evaporated under reduced pressure to obtain the final product. Purity was confirmed by 1H NMR. If significant impurities are observed, the product can be recrystallized, most typically in isopropanol or toluene.

Reference： [1]Patent: WO2008/84300,2008,A1 .Location in patent: Page/Page column 35
[2],2019,vol. 10,p. 1958 - 1965
[3]Heterocycles,1992,vol. 34,p. 747 - 756
[4]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5870 - 5884
[5]Journal of Heterocyclic Chemistry,2013,vol. 50,p. E126-E130
[6]Synthetic Communications,2013,vol. 43,p. 2603 - 2614
[7]RSC Advances,2016,vol. 6,p. 75651 - 75663
[8]Tetrahedron Letters,2012,vol. 53,p. 191 - 195
[9]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1746 - 1749
[10]Chinese Journal of Chemistry,2012,vol. 30,p. 1339 - 1344
[11]Archiv der Pharmazie,2014,vol. 347,p. 89 - 95
[12]Journal of the Chinese Chemical Society,2017,vol. 64,p. 1408 - 1416
[13]Tetrahedron Letters,2019,vol. 60,p. 72 - 74
[14]Chemistry and biodiversity,2019,vol. 16

11
[ 2632-14-6 ]
[ 56008-40-3 ]
[ 142818-16-4 ]

Reference： [1]Heterocycles,1992,vol. 34,p. 747 - 756

12
[ 2632-14-6 ]
[ 113258-86-9 ]
[ 140420-15-1 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 67 - 78

13
[ 2632-14-6 ]
[ 57509-01-0 ]
[ 96885-28-8 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 823 - 828
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1456 - 1461

14
[ 2632-14-6 ]
[ 93703-25-4 ]
[ 106087-28-9 ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 122 - 125
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 187 - 190

15
[ 2632-14-6 ]
[ 78394-94-2 ]
[ 78394-98-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 564 - 568
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 653 - 657

16
[ 2632-14-6 ]
[ 127-08-2 ]
2-acetoxy-1-(4-ethyl-phenyl)-ethanone [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1966,vol. 33,p. 265 - 276

17
[ 2632-14-6 ]
2-<4-Ethyl-phenyl>-2-oxo-diazo-ethan [ No CAS ]

Reference： [1]Angewandte Chemie,1965,vol. 77,p. 678 - 679

19
[ 1632-74-2 ]
[ 2632-14-6 ]
[ 505097-16-5 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 9933 - 9940

20
[ 2632-14-6 ]
3,5,5-Trimethyl-6-(4-bromophenyl)-2,3,5,6-tetrahydropyran-2,4-dione [ No CAS ]
6-(4-bromo-phenyl)-3-[2-(4-ethyl-phenyl)-2-oxo-ethyl]-3,5,5-trimethyl-dihydro-pyran-2,4-dione [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2001,vol. 37,p. 1512 - 1513

21
[ 673-22-3 ]
[ 2632-14-6 ]
[ 878196-25-9 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1016 - 1022

22
[ 89-95-2 ]
[ 2632-14-6 ]
[ 887908-66-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3643 - 3653

23
[ 168762-61-6 ]
[ 2632-14-6 ]
C₁₈H₂₅NO₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1746 - 1749

24
[ 104-13-2 ]
[ 2632-14-6 ]
5-butyl-2-(4-ethylphenyl)indole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 5122 - 5136

25
[ 2632-14-6 ]
[ 78394-83-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 564 - 568
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 653 - 657

26
[ 2632-14-6 ]
[ 887908-69-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3643 - 3653

27
[ 2632-14-6 ]
1-[benzofuran-2-yl-(4-ethyl-phenyl)-methyl]-1H-[1,2,4]triazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3643 - 3653

28
[ 2632-14-6 ]
4-[benzofuran-2-yl-(4-ethyl-phenyl)-methyl]-4H-[1,2,4]triazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3643 - 3653

29
[ 2632-14-6 ]
[ 878196-33-9 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1016 - 1022

30
[ 2632-14-6 ]
1-[(6-methoxybenzofuran-2-yl)-(4-ethylphenyl)methyl]-1H-1,2,4-triazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1016 - 1022

31
[ 2632-14-6 ]
[ 505097-26-7 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 9933 - 9940

32
[ 2632-14-6 ]
[ 505097-31-4 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 9933 - 9940

33
[ 2632-14-6 ]
2-{3-[6-(4-ethylphenyl)-2-methylpyrrolo[1,2-b]pyridazin-7-yl]-6-oxo-1,6-dihydro-1-pyridazinyl}acetic acid [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 9933 - 9940

34
[ 2632-14-6 ]
[ 505097-32-5 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 9933 - 9940

35
[ 2632-14-6 ]
[ 106087-38-1 ]

Reference： [1]Pharmaceutical Chemistry Journal,1986,vol. 20,p. 122 - 125
Khimiko-Farmatsevticheskii Zhurnal,1986,vol. 20,p. 187 - 190

36
[ 2632-14-6 ]
[ 96885-66-4 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 823 - 828
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1456 - 1461

37
[ 2632-14-6 ]
[ 96885-60-8 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 823 - 828
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1456 - 1461

38
[ 2632-14-6 ]
[ 96885-25-5 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 823 - 828
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1456 - 1461

39
[ 2632-14-6 ]
[ 96902-19-1 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 823 - 828
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1456 - 1461

40
[ 2632-14-6 ]
2-Benzyl-4-(4-ethyl-phenyl)-1,2,3,4-tetrahydro-isoquinolin-4-ol [ No CAS ]

Reference： [1]Heterocycles,1992,vol. 34,p. 747 - 756

41
[ 2632-14-6 ]
[ 140420-11-7 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 67 - 78

42
[ 2632-14-6 ]
4-(4-Ethyl-phenyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-ol [ No CAS ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 67 - 78

43
[ 2632-14-6 ]
[ 39644-63-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1972,vol. 37,p. 3950 - 3955

44
[ 504-75-6 ]
[ 2632-14-6 ]
[ 1094655-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	2. Preparation of 1-(4-ethylphenyl)-2-imidazolylethan-1-one 1 mmol of <strong>[2632-14-6]2-bromo-1-(4-ethylphenyl)ethan-1-one</strong> in acetonitrile was added drop wise to 5.5 mmol imidazoline in acetonitrile at room temperature for fourteen hours. The reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The solution was extracted three times with ethyl acetate and dried over sodium sulfate to obtain 1 -(4-ethylphenyl)-2-imidazolylethan-1 -one.

Reference： [1]Patent: US2002/156087,2002,A1

Yield	Reaction Conditions	Operation in experiment
		Typical examples of the halomethyl phenyl ketones (2) wherein X is a bromine atom include 2 -bromoacetophenone, ... 2-bromo-4'-chloroacetophenone, 2-bromo-4'-bromoacetophenone, 2-bromo-4'-fluoroacetophenone, 2-bromo-4'-methylacetophenone, 2-bromo-4'-ethylacetophenone, 2-bromo-4'-propylacetophenone, 2-bromo-4'-butylacetophenone, 2-bromo-4'-methoxyacetophenone, ...

46
[ 2632-14-6 ]
[ 103793-25-5 ]

Yield	Reaction Conditions	Operation in experiment
38%	With 1-methyl-1H-imidazole; In diethyl ether;	EXAMPLE 5 1-Methyl-3-[2-(4-ethylphenyl)-2-oxoethyl]-1H-imidazolium bromide A solution of 4.41 g (0.019 mol) of <strong>[2632-14-6]1-bromo-2-(4-ethylphenyl)-2-oxoethane</strong> and 1.65 g (0.02 mol) of 1-methylimidazole in 40 ml of diethyl ether was stirred at room temperature for approximately 18 hours. The reaction solvent was decanted, and the residue was washed with diethyl ether and dissolved in a small amount of acetonitrile. The resulting solution was diluted with a small amount of ethyl acetate, whereupon a brown precipitate formed. The solid was collected and recrystallized from acetonitrile/ethyl acetate to provide 2.26 g of 1-methyl-3-[2-(4-ethylphenyl)-2-oxoethyl]-1H-imidazolium bromide as fine yellow brown needles. (38% yield) mp=177-179 C. Analysis calculated for C14 H17 BrN2 O. Theory: C, 54.38; H, 5.54; N, 9.06; Br, 25.84; Found: C, 54.13; H, 5.81; N, 9.04; Br, 26.05.

Reference： [1]Patent: US4609670,1986,A

47
4-{6-fluoro-5-[(methylamino)carbonyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}piperidinium trifluoroacetate [ No CAS ]
[ 2632-14-6 ]
[ 1037834-12-0 ]

Yield	Reaction Conditions	Operation in experiment
98%		Example No. 9; 1-t2-(4-ethylphenyl)-2-oxoethyl]-4-{6-fluoro-5-[(methylamino)carbonyl]-2-oxo-2,3- dihydro-1H-benzimidazol-1-yl}piperidinium chloride; <n="38"/>4-{6-fluoro-5-[(methylamino)carbonyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1- yljpiperidinium trifluoroacetate (20 g, 31 mmol) was dissolved in 100 mL N1N- dimethylformamide, added triethylamine (25.9 mL, 186 mmol) followed by the addition of <strong>[2632-14-6]2-bromo-1-(4-ethylphenyl)ethanone</strong> (11 g, 37 mmol) which was dissolved in 20 mL N1N- dimethylformamide. The reaction mixture was stirred at ambient temperature for 1 hour. An aqueous solution of 5% sodium bicarbonate (300 ml) was added slowly. The desired compound was extracted with dichloromethane (400 mL), and the organic layer was washed with water and brine, dried with magnesium sulfate, filtered. The filtrate was concentrated in vacuo. The desired product was purified by column chromatography eluting with 100% ethyl acetate for, then 0-30% methanol in ethyl acetate. Desired spot eluted with impurities and some of the orange color. All fractions containing product were concentrated in vacuo to a light orange solid. This was further purified by column chromatography eluting with a gradient of 1-40% methanol in ethyl acetate. A set of fractions were combined that look pure by TLC and concentrated in vacuo. Suspended were solids in 100 mL ethyl acetate at 5O0C and was cooled to ambient temperature. Solids were filtered off washed with cold ethyl acetate. The resultant solid was dissolved in 50 mL methanol and 100 mL dichloromethane, and subsequently cooled to O0C through which hydrogen chloride gas was bubbled for 1 minute. The solution was concentrated together with 50 mL methanol, and subsequently re-suspended in 50 mL methanol, suspended at 400C for 5 minutes, to which was added 300 mL of diethyl ether. Solids were filtered off to yield the title compound. (5.92 g, 42%) APCI+ 439.21 ; Anal. HPLC Retention time = 13.5 minutes (98% pure). 1H NMR (DMSO-Gf6) delta 11.2 (s, 1 H), 10.2 (s, 1 H), 8.00 (m, 1 H), 7.91 (d, 2 H), 7.52 (d, 1 H), 7.43 (d, 2 H), 7.23 (d, 1 H), 5.04 (m, 2 H), 4.57 (m, 1 H), 3.64 (m, 2 H), 3.3 (m, 2 H), 2.8-2.63 (m, 7 H), 1.92 (m, 2 H), 1.18 (t, 3 H).

Reference： [1]Patent: WO2008/84300,2008,A1 .Location in patent: Page/Page column 35-36

48
[ 3770-50-1 ]
[ 2632-14-6 ]
[ 1049318-37-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1083 - 1087

49
[ 2632-14-6 ]
[ 23269-89-8 ]
[ 1104526-76-2 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2008,vol. 58,p. 510 - 514

50
[ 1477-50-5 ]
[ 2632-14-6 ]
[ 1002234-62-9 ]

Reference： [1]Synthetic Communications,2008,vol. 38,p. 3884 - 3893

51
[ 110-86-1 ]
[ 2632-14-6 ]
[ 88284-48-4 ]
[ 1133726-76-7 ]

Reference： [1]Synlett,2008,p. 3115 - 3120

52
[ 110-86-1 ]
[ 2632-14-6 ]
4,5-dimethyl-2-(trimethylsilyl)phenyl triflate [ No CAS ]
[ 1133726-77-8 ]

Reference： [1]Synlett,2008,p. 3115 - 3120

53
[ 36193-65-4 ]
[ 2632-14-6 ]
[ 1178572-09-2 ]

Reference： [1]Synlett,2009,p. 1463 - 1465

54
[ 2632-14-6 ]
[ 5114-84-1 ]
[ 1228793-52-9 ]

Reference： [1]Synthesis,2010,p. 1009 - 1013

55
[ 860019-99-4 ]
[ 2632-14-6 ]
C₁₈H₁₉N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A stirred mixture of 3-amino-6-propoxypyridazine 3 (4.50g, 29.4mmol), 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone 11 (8.03g, 29.4mmol) and EtOH (280mL) was heated at reflux for 2.5 hours. The mixture was cooled and NaHCO3 (2.50g, 30mmol) was added. The mixture was stirred at room temperature for 15 hours, heated at reflux for 1 hour, then cooled and evaporated. The residue was extracted with CHCl3 (150mL) and the extract washed with saturated, aqueous NaCl solution (50mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography over silica gel. Elution with 1-2% MeOH in CH2Cl2 afforded a green/brown solid. Treatment with decolourising charcoal and recrystallization from cyclohexane gave 6f (3.95g, 41%) as pale green crystals, m.p. 82.5-84C. 1H NMR (CDCl3) ? 1.06 (3H, t, J=7.2Hz), 1.75-1.94 (2H, m), 3.47 (3H, s), 3.74-3.81 (2H, m), 4.14-4.21 (2H, m), 4.27 (2H, t, J=6.6Hz), 6.68 (1H, d, J=9.3Hz), 7.00 (2H, d, J=8.8Hz), 7.76-7.88 (3H, m), 7.94 (1H, s). MS (APCI+) m/z 328 (M+H, 100%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4160 - 4163

56
[ 2632-14-6 ]
[ 332073-80-0 ]
[ 1314895-24-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2011,vol. 47,p. 82 - 89

57
[ 2632-14-6 ]
[ 524057-23-6 ]
[ 1314895-26-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2011,vol. 47,p. 82 - 89

58
[ 2632-14-6 ]
[ 95-54-5 ]
[ 1350516-03-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium fluoride on basic alumina; at 20℃; for 2h;	General procedure: A mixture of 1,2-diamine (1 mmol) and alpha-bromo ketone (1 mmol) was intimately mixed with pre-activated KF-alumina (1:4) (0.5 g) (Basic; Grade: Brockmann 1, and activated by heating under vacuum at 150 C until bubbling ceases and then cooled to room temperature under vacuum) and stirred the solid mixture with a magnetic spin bar at room temperature for hours as indicated in refPreviewPlaceHolderTable 3. After the reaction was complete, the solid mixture washed with diethyl ether (3 × 10 mL) and the solid was filtered off. The filtrate was concentrated and passed through a short column of silica gel to afford the quinoxalines. The desired product was pure on TLC and characterized by spectral (1H and 13C NMR) data and compared to those reported.
	With polymeric resin-bound hexafluorophosphate ion; In methanol; water; at 20℃; for 6h;	General procedure: In a typical experimental procedure, o-phenlylenediamine and alpha-bromo ketone in 1:1 molar ratios was taken in a 100 mL round bottom flask. To this water-methanol (1:1) and 100 mg PHP was admixed. The reaction mixture was then allowed to stir with magnetic spinning bar, after some time a yellowish mass appeared which settles down like a precipitate after the completion of the reaction (checked by TLC). It was then filtered; the solid reaction mixture was dissolved with dichloromethane (25 mL) and evaporated under vacuum. The crude product was then crystallised from ethanol. The desired product was pure on TLC and characterized by spectral (IR, 1H and 13C NMR) data and compared to those reported in literature.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 6597 - 6602
[2]Tetrahedron Letters,2012,vol. 53,p. 6483 - 6488,6

59
[ 2632-14-6 ]
[ 1160554-10-8 ]

Reference： [1]Chinese Journal of Chemistry,2012,vol. 30,p. 1339 - 1344

60
[ 2632-14-6 ]
[ 1243257-32-0 ]

Reference： [1]Chinese Journal of Chemistry,2012,vol. 30,p. 1339 - 1344

61
[ 2632-14-6 ]
[ 111-42-2 ]
C₁₄H₂₂BrNO₃ [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2012,vol. 30,p. 1339 - 1344

62
[ 2632-14-6 ]
[ 1396790-09-2 ]