[ CAS No. 85-29-0 ] {[proInfo.proName]}

Name: 85-29-0|(2-Chlorophenyl)(4-chlorophenyl)methanone|98%
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SKU: A104037
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2D 3D

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Quality Control of [ 85-29-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 85-29-0 ]

SDS Specification

Alternatived Products of [ 85-29-0 ]

Product Details of [ 85-29-0 ]

CAS No. :	85-29-0	MDL No. :	MFCD00038744
Formula :	C₁₃H₈Cl₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YXMYPHLWXBXNFF-UHFFFAOYSA-N
M.W :	251.11	Pubchem ID :	66558
Synonyms :

Calculated chemistry of [ 85-29-0 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.34
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.62
Log Po/w (XLOGP3) :	4.38
Log Po/w (WLOGP) :	4.22
Log Po/w (MLOGP) :	4.05
Log Po/w (SILICOS-IT) :	4.65
Consensus Log Po/w :	3.99

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.58
Solubility :	0.00662 mg/ml ; 0.0000263 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.45
Solubility :	0.00881 mg/ml ; 0.0000351 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.1
Solubility :	0.000199 mg/ml ; 0.000000794 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 85-29-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 85-29-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 85-29-0 ]

[ 85-29-0 ] Synthesis Path-Downstream 1~88

1
[ 17624-36-1 ]
[ 85-29-0 ]
[ 101875-98-3 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 472,476

2
[ 637-87-6 ]
[ 85-29-0 ]
[ 88545-09-9 ]

Reference： [1]Chemische Berichte,1906,vol. 39,p. 3278

3
[ 85-29-0 ]
[ 75-16-1 ]
[ 85072-16-8 ]

Reference： [1]Analytical Chemistry,1952,vol. 24,p. 702,704

4
[ 85-29-0 ]
[ 92206-72-9 ]
[ 114303-26-3 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 591,595

5
[ 85-29-0 ]
[ 43171-49-9 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20℃; for 3h;	(1) (2-Chlorophenyl)(4'-chlorophenyl)methanol To a solution of <strong>[85-29-0]2,4'-dichlorobenzophenone</strong> (10.0 g, 39.8 mmol) in ethanol (100 ML) and THF (100 ML) was added sodium borohydride (753 mg, 19.9 mmol), the mixture was stirred at room temperature for 3 hours, and the solvent was distilled off under reduced pressure.. The residue was poured into water, and was extracted with ethyl acetate.. The extracted solution was washed with water, was dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain the titled compound as oil. 9.43 g (93.4%) 1H-NMR (CDCl3) delta; 2.39 (1H, d, J = 3.8 Hz), 6.20 (1H, d, J = 3.8 Hz), 7.18 to 7.58 (8H, m)
78%		To a stirred solution of 2, 4'-dichlorobenzophenone (239 mmol) in methanol (400 mL) was added sodium borohydride (119 mmol) portionwise at 0C. Reaction mixture was warmed to room temperature and stirred for 1 hour, then quenched with water and the methanol was removed under reduced pressure. The residue was diluted with dichloromethane (400 mL) and washed with water and brine, dried (MGS04) and concentrated in vacuo to yield the product as an orange oil (47.1 g, 78%). NMR (400MHZ, D6-DMSO) 5H 5.99 (1H, d, J 4. 5 Hz), 6.16 (1H, d, J 4. 5 Hz), 7.35 (7H, m), 7.66 (1H, m).
78%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 1h;	To a stirred solution OF 2, 4 -DICHLOROBENZOPHENONE (239 mmol) in methanol (400 ML) was added sodium borohydride (119 mmol) portionwise at 0C. The reaction mixture was warmed to room temperature and stirred for 1 hour, then quenched with water and the methanol was removed under reduced pressure. The residue was diluted with dichloromethane (400 mL) and washed with water and brine, dried (MGS04) and concentrated in vacuo to yield the product as an orange oil (47.1 g, 78%). NMR (400MHZ, D-DMSO) 6H 5.99 (1H, d, J4. 5 Hz), 6.16 (1H, d, J4. 5 Hz), 7. 35 (7H, m), 7.66 (1H, m)

78%	With sodium tetrahydroborate; In methanol; for 1.7h;	General procedure: To a stirred solution of 4a (29.80 g, 118.22 mmol) in MeOH (500 mL) was added portionwise sodium borohydride (2.24 g, 59.17 mmol) over 15 minutes. Stirring was continued for 1.5 hr, where upon the solvents were removed in vacuo. Water (500 mL) was added and the mixture extracted with EtOAc (3 × 250 mL). The organic extracts were washed successively with water (500 mL) and brine (500 mL), combined and evaporated in vacuo. The crude product was sonicated with n-hexane and the pure product collected by filtration to give the alcohol 5a (26.82 g, 89%) as a beige powder.
	With sodium borohydrid; In sodium hydroxide; ethanol;	Step A Synthesis of (2-chlorophenyl)(4-chlorophenyl)methanol as an intermediate Under a nitrogen atmosphere, 1.7 grams (0.044 mole) of sodium borohydride pellets was added to 100 ml of stirred ethanol. To this was added 10.0 grams (0.040 moles) of <strong>[85-29-0]2,4'-dichlorobenzophenone</strong> in one portion. Upon completion of the addition the reaction mixture was stirred at ambient temperature for about 18 hours. After this time the ethanol was removed under reduced pressure, and the resulting residue was taken up in 250 mL of aqueous 5% sodium hydroxide solution. The solution was extracted with two 100 mL portions of diethyl ether. The combined ether extracts were washed with aqueous saturated sodium chloride solution. The organic layer was filtered and the filtrate concentrated under reduced pressure, yielding 9.5 grams of (2-chlorophenyl)(4-chlorophenyl)methanol. The NMR spectrum was consistent with the proposed structure.

Reference： [1]Synthetic Communications,2008,vol. 38,p. 1703 - 1717
[2]Patent: EP1437344,2004,A1 .Location in patent: Page 47
[3]Patent: WO2004/96763,2004,A1 .Location in patent: Page 29
[4]Patent: WO2004/96794,2004,A1 .Location in patent: Page 23-24
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 901 - 906
[6]Journal of the American Chemical Society,1958,vol. 80,p. 2896
[7]Journal of the American Chemical Society,1961,vol. 83,p. 429 - 434
[8]Patent: US2007,2001,H1
[9]Letters in drug design and discovery,2010,vol. 7,p. 661 - 664
[10]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1859 - 1865

6
[ 85-29-0 ]
[ 52094-02-7 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 2896

7
[ 85-29-0 ]
[ 52094-02-7 ]
1,2-bis-(2-chloro-phenyl)-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 1254
[2]Journal of the American Chemical Society,1947,vol. 69,p. 1254

8
[ 85-29-0 ]
dichloro-(2-chloro-phenyl)-(4-chloro-phenyl)-methane [ No CAS ]

Reference： [1]American Chemical Journal,1903,vol. 30,p. 395

9
[ 85-29-0 ]
[ 87424-35-9 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546

10
[ 85-29-0 ]
[ 6633-46-1 ]

Reference： [1]Patent: US2377751,1940,

11
[ 3424-82-6 ]
[ 85-29-0 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 1591,1599

12
[ 52094-02-7 ]
[ 85-29-0 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 2222
[2]Tetrahedron Letters,1994,vol. 35,p. 5833 - 5836

13
[ 108-90-7 ]
[ 74-11-3 ]
[ 85-29-0 ]
[ 90-98-2 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 2232 - 2235
[2]Industrial and Engineering Chemistry,1935,vol. 27,p. 1398
Chemisches Zentralblatt,1936,vol. 107,p. 4004

14
[ 85-29-0 ]
[ 105-56-6 ]
[ 62715-63-3 ]

Reference： [1]Journal of Organic Chemistry,1950,vol. 15,p. 381,386, 389

15
[ 85-29-0 ]
[ 119-26-6 ]
[ 7478-72-0 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 1591,1599

16
[ 917-64-6 ]
[ 85-29-0 ]
[ 39274-24-3 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 98 - 100
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 163 - 166
[2]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 1008 - 1015

17
[ 85-29-0 ]
[ 75-26-3 ]
[ 93011-56-4 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 1008 - 1015

18
[ 4595-59-9 ]
[ 85-29-0 ]
[ 60168-88-9 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1359 - 1365

19
[ 85-29-0 ]
[ 1937-19-5 ]
[ 146470-10-2 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 758 - 764

20
[ 85-29-0 ]
[ 72189-68-5 ]
[ 146470-36-2 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 758 - 764

21
[ 14835-94-0 ]
[ 85-29-0 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 98 - 100
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 163 - 166

22
[ 609-65-4 ]
[ 108-90-7 ]
[ 85-29-0 ]
[ 5293-97-0 ]
[ 90-98-2 ]

Reference： [1]Chemistry Letters,1982,p. 1229 - 1232
[2]Chemistry Letters,1982,p. 1229 - 1232

23
[ 609-65-4 ]
[ 85-29-0 ]
[ 5293-97-0 ]
[ 90-98-2 ]

Reference： [1]Chemistry Letters,1982,p. 1229 - 1232

24
[ 122-01-0 ]
[ 108-90-7 ]
[ 85-29-0 ]
[ 7498-66-0 ]
[ 90-98-2 ]

Reference： [1]Chemische Berichte,1983,vol. 116,p. 1195 - 1208

25
[ 85-29-0 ]
[ 105-39-5 ]
[ 34877-75-3 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 4597 - 4601
[2]Canadian Journal of Chemistry,1973,vol. 51,p. 3820 - 3825

26
[ 85-29-0 ]
[ 151-50-8 ]
<NH4>2CO3 [ No CAS ]
[ 96315-38-7 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 4152,4154

27
2.4'.α.α-tetrachloro-diphenylmethane [ No CAS ]
4.4'.α.α-tetrachloro-diphenylmethane [ No CAS ]
[ 85-29-0 ]
[ 90-98-2 ]

Reference： [1]American Chemical Journal,1903,vol. 30,p. 395

28
[ 7446-70-0 ]
[ 108-90-7 ]
[ 74-11-3 ]
[ 85-29-0 ]
[ 90-98-2 ]

Reference： [1]Industrial and Engineering Chemistry,1935,vol. 27,p. 1398
Chemisches Zentralblatt,1936,vol. 107,p. 4004

29
[ 108-90-7 ]
p-chloro-benzoyl chloride [ No CAS ]
[ 85-29-0 ]
[ 90-98-2 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1902,vol. 21,p. 25
Recueil des Travaux Chimiques des Pays-Bas,1906,vol. 25,p. 384
[2]Recueil des Travaux Chimiques des Pays-Bas,1906,vol. 25,p. 384

30
[ 56-23-5 ]
[ 7446-70-0 ]
[ 108-90-7 ]
[ 85-29-0 ]
[ 90-98-2 ]

Reference： [1]American Chemical Journal,1903,vol. 30,p. 395

Yield	Reaction Conditions	Operation in experiment
97.8%		EXAMPLE 5 The reaction was carried out as in Example 1 with the following compounds and under the following conditions: 49.1 g (yield: 97.8%) of 2,4'-dichlorobenzophenone with 97% purity was recovered.
55%		EXAMPLE 3 A procedure analogous to Example 1 is employed, with the following compounds and conditions: 7 g (yield=55%) of a mixture essentially consisting of 4,4'-dichlorobenzophenone and 2,4'-dichlorobenzophenone (analyses by gas phase chromatography and infrared) is obtained.

33
[ 108-90-7 ]
o-chloro-benzoyl chloride [ No CAS ]
[ 85-29-0 ]

Reference： [1]American Chemical Journal,1903,vol. 30,p. 395

34
[ 7647-01-0 ]
[ 85-29-0 ]
[ 108-88-3 ]
amalgamated zinc [ No CAS ]
[ 52094-02-7 ]
1,2-bis-(2-chloro-phenyl)-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 1254

35
[ 85-29-0 ]
p-chloro-iodobenzene [ No CAS ]
[ 861532-79-8 ]

Reference： [1]Chemische Berichte,1906,vol. 39,p. 3278

36
[ 32315-10-9 ]
[ 108-90-7 ]
[ 85-29-0 ]
[ 90-98-2 ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 2361 - 2367
[2]Synthetic Communications,2004,vol. 34,p. 4249 - 4256

37
[ 109-72-8 ]
[ 85-29-0 ]
(2-butyl-phenyl)-(4-chloro-phenyl)-methanone [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4395 - 4398

38
[ 85-29-0 ]
[ 77008-62-9 ]

39
[ 85-29-0 ]
[ 90284-72-3 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 98 - 100
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 163 - 166

40
[ 53-19-0 ]
[ 85-29-0 ]

Reference： [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 98 - 100
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 163 - 166

41
[ 85-56-3 ]
[ 85-29-0 ]

Reference： [1]Industrial and Engineering Chemistry,1935,vol. 27,p. 1398
Chemisches Zentralblatt,1936,vol. 107,p. 4004

42
[ 789-02-6 ]
[ 85-29-0 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 2222
[2]Journal of the American Chemical Society,1945,vol. 67,p. 1591,1599

43
[ 85-29-0 ]
[ 39274-24-3 ]

Reference： [1]Analytical Chemistry,1952,vol. 24,p. 702,704

44
[ 36692-27-0 ]
[ 85-29-0 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 1591,1599

45
[ 85-29-0 ]
ethyl-(2,4',4''-trichloro-trityl)-ether [ No CAS ]

Reference： [1]Chemische Berichte,1906,vol. 39,p. 3278

46
[ 85-29-0 ]
[ 93694-04-3 ]

Reference： [1]Chemische Berichte,1906,vol. 39,p. 3278
[2]Chemische Berichte,1906,vol. 39,p. 3278

47
[ 85-29-0 ]
[ 861532-79-8 ]

Reference： [1]Chemische Berichte,1906,vol. 39,p. 3278

48
[ 85-29-0 ]
bis-(2,4',4''-trichloro-trityl)-peroxide [ No CAS ]

Reference： [1]Chemische Berichte,1906,vol. 39,p. 3278

49
[ 10291-39-1 ]
[ 85-29-0 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 1591,1599

50
[ 85-29-0 ]
4-[2-(2-chloro-phenyl)-2-(4-chloro-phenyl)-vinyl]-benzamidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 591,595

51
[ 85-29-0 ]
[ 96662-54-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546

52
[ 85-29-0 ]
[ 13312-58-8 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 4597 - 4601

53
[ 85-29-0 ]
[ 34113-46-7 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 4597 - 4601

54
[ 85-29-0 ]
[ 92291-62-8 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 4597 - 4601

55
[ 85-29-0 ]
meso-α,α'-2,4'-Tetrachlor-bibenzyl [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 4597 - 4601

56
[ 85-29-0 ]
[ 3424-82-6 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 1008 - 1015

57
[ 85-29-0 ]
[ 14835-94-0 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 1008 - 1015

58
[ 85-29-0 ]
[ 97212-40-3 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 1008 - 1015

59
[ 85-29-0 ]
[ 69537-88-8 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 1008 - 1015

60
[ 609-65-4 ]
[ 108-90-7 ]
[ 85-29-0 ]
[ 5293-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	iron(III) chloride; at 176℃; for 0.341667h;Irradiation;Product distribution / selectivity;	In these examples, the activation, under a microwave field, of acylation reactions on a deactivated aromatic substrate such as chlorobenzene is demonstrated. The conditions of examples 32 to 35 are reproduced. The aromatic substrate is chlorobenzene in all the examples, with a molar ratio with respect to the acylating agent of 1:1 for examples 36 and 37; and of 2:1 for example 38. The para-isomer of the aromatic ketone obtained is the majority isomer (94 to 99%) over the ortho-isomer.

Reference： [1]Patent: US6348631,2002,B1 .Location in patent: Page column 18,19

61
[ 85-29-0 ]
[ 90155-46-7 ]
[ 43171-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In isopropyl alcohol; benzene;	COMPARATIVE EXAMPLE 7 Asymmetric hydrogenation of <strong>[85-29-0]2,4'-dichlorobenzophenone</strong> Into a 100 ml stainless autoclave were fed a 0.2M solution of potassium hydroxide in 2-propanol (1.4 ml, containing 0.28 mmol of potassium hydroxide), (R,R)-diphenylethylenediamine (4.03 mg, 0.019 mmol), <strong>[85-29-0]2,4'-dichlorobenzophenone</strong> (1.26 g, 5.0 mmol), 2-propanol (3.31 ml), benzene (1.37 ml) and Ru2 Cl4 [(R)-BINAP]2 NEt3 (8.45 mg, 0.005 mmol) under a nitrogen atmosphere. Then hydrogen gas was supplied thereinto so as to achieve a hydrogen pressure of 50 atm. After stirring at a reaction temperature of 50 C. for 20 hours, the reaction mixture was returned to ordinary temperatures and then concentrated under reduced pressure. 1.30 g of the residue thus obtained was purified by silica gel column chromatography (developer: hexane/ethyl acetate=4/1 to 2/1 by volume) to thereby give optically active 2,4'-dichlorobenzhydrol (1.183 g, yield: 93.4%). The optical purity of this 2,4'-dichlorobenzhydrol measured by high performance liquid chromatography was 60.62% e.e.

Reference： [1]Patent: US5780692,1998,A

62
[ 67-71-0 ]
[ 85-29-0 ]
[ 1806-23-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium fluoride; In water; isopropyl alcohol; benzene;	EXAMPLE 7 To a mixture of 10.1 g (0.04 mols) of <strong>[85-29-0]2,4'-dichlorobenzophenone</strong>, 4.6 g (0.08 mols) of potassium fluoride and 20 g of dimethyl sulfone were 5 ml of benzene added and water in the reaction system was removed together with benzene by azeotropy. The reaction was carried out under nitrogen atmosphere at temperatures of 230-240 C. while stirring for 11 hours. After cooling the reaction product was extracted under heating twice with 20 ml of isopropanol. The extracts together were placed to cool and thus, 7.5 g of 2-chloro-4'-fluorobenzophenone were obtained. Yield 80%, M.P. 60-61 C. Pure product was obtained from recrystallization with isopropanol. M.P. 60-61 C.

Reference： [1]Patent: US4453009,1984,A

63
[ 1039167-68-4 ]
[ 85-29-0 ]
[ 1039166-03-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example 55 (RS)-N-[(2-Chlorophenyl)(4-chlorophenyl)methyl]-2-oxo-2-(1'H,3H-spiro[2-benzofuran-1,4'-piperidin]-1'-yl)ethanamine 2-Oxo-2-(1'H,3H-spiro[2-benzofuran-1,4'-piperidin]-1'-yl)ethanamine (50 mg, 0.203 mmol) and <strong>[85-29-0](4-chloro-phenyl)-(2-chloro-phenyl)-methanone</strong> (51 mg, 0.203 mmol) were dissolved in toluene (1 mL). Tetraisopropyl orthotitanate (0.12 mL, 0.406 mmol) was added and the mixture was heated in a sealed tube in a microwave oven at 140 C. for 15 min. After cooling, ethanol (1 mL) and sodium cyanoborohydride (15 mg) were added and the reduction was allowed to proceed at 20 C. over night. Next day, water (0.2 mL) was added and shaking was continued for 24 h to precipitate the titanium oxides. The suspension was filtered through dicalite and the solid rinsed with EtOH (5 mL). The filtrate was recuperated and evaporated to dryness. The residue was dissolved in DMSO (1 mL) and then directly purified by preparative HPLC on a YMC-AQ column with a gradient of acetonitrile acid (30-95% in 15 min.) in aqueous 0.05% formic. The fractions with the correct mass were collected and evaporated to dryness to afford the title compound. MS: m/z=482 [M+H]+.

Reference： [1]Patent: US2008/171759,2008,A1 .Location in patent: Page/Page column 39-40

64
[ 85-29-0 ]
[ 705-29-3 ]
[ 1241941-39-8 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 4665 - 4668

65
[ 85-29-0 ]
[ 352-11-4 ]
1-(2-chlorophenyl)-1-(4-chlorophenyl)-2-(4-fluorophenyl)ethanol [ No CAS ]

Reference： [1]Synthesis,2010,p. 3802 - 3810

66
[ 85-29-0 ]
(E)-1-((2-chlorophenyl)(4-chlorophenyl)methyl)-4-styrylpiperazine dihydrochloride [ No CAS ]

Reference： [1]Letters in drug design and discovery,2010,vol. 7,p. 661 - 664

67
[ 85-29-0 ]
[ 61023-86-7 ]

Reference： [1]Letters in drug design and discovery,2010,vol. 7,p. 661 - 664

68
[ 488149-34-4 ]
[ 873-77-8 ]
[ 85-29-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 5 - 25℃;Inert atmosphere;	General procedure: A solution of 3a (23.74 g, 118.33 mmol) was dissolved in dry THF (500 mL) in a 3-necked flask equipped with thermometer, nitrogen bubbler and pressure-equalising dropping funnel. The flask was purged with nitrogen, and cooled to 5 C (internal temperature). The dropping funnel was charged with 4-chlorophenylmagnesium bromide (1.0 M in Et2O; 153.8 mL, 153.80 mmol) and the reagent added to the reaction flask dropwise over 15 minutes, during which time the temperature rose to 8 C. Stirring was continued for 19 h, during which time the temperature rose to ambient. Hydrochloric acid (2.0 M in H2O; 400 mL) was added slowly and the mixture stirred vigorously for 30 minutes. The mixture was adjusted to pH 8 by cautious addition of solid NaHCO3, water (500 mL) added, and the mixture extracted with EtOAc (3 × 500 mL). The organic extracts were washed successively with water (500 mL) and brine (500 mL), combined, dried (MgSO4) and evaporated to dryness to give the ketone 4a (29.8 g, 100%) as a yellow oil.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 901 - 906

69
[ 85-29-0 ]
[ 791118-68-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 901 - 906

70
[ 85-29-0 ]
[ 791118-70-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 901 - 906

71
[ 85-29-0 ]
3-(2,4'-dichlorobenzhydryloxy)azetidine hydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 901 - 906

72
[ 85-29-0 ]
[ 1026410-64-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 901 - 906

73
[ 289-95-2 ]
[ 85-29-0 ]
[ 1374583-73-9 ]