Name: 13633-25-5|1-Bromo-4-phenylbutane|96%
Brand: Ambeed
SKU: A906363
Price: 14.0 USD
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1
[ 3360-41-6 ]
[ 13633-25-5 ]

Yield	Reaction Conditions	Operation in experiment
99.6%	With hydrogen bromide; for 12h;Irradiation; Reflux;	step 1,10 g of 4-phenylbutanol and 44 g of hydrobromic acid were sequentially added to a 250 m1 three-necked flask.2 g of POM-C3N4 catalyst, the system is light yellow and mechanically stirred.Protected from light, heated to reflux for 12 h;Step 2After the reaction, the system was yellow and viscous and cooled to room temperature.Adjust the pH of the system with saturated Na2CO3 solution = 7, stir for 30min, after liquid separation,The organic phase is extracted with dichloromethane until the aqueous layer is colorless and transparent;Step 3.After the above extract phase is dried over anhydrous sodium sulfate,The dichloromethane was evaporated to give a pale yellow product, 1-bromo-4-phenylbutane.
95%		A solution of l-phenyl-4-butanol (1.05 g, 7.0 mmol) in anhydrous CH2Cl2 (20 mL) was treated with CBr4 (2.55 g, 7.6 mmol) and was stirred for 5 min at 25 C. PPh3 (2.02 g, 7.7 mmol) in anhydrous CH2Cl2 (6 mL) was added dropwise and was stirred for 1 h at 25 C. The reaction mixture was quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. Column chromatography (SiO2, 5.5 x 9 cm, 3% EtOAc-hexanes) afforded l-phenyl-4- bromobutane (1.41 g, 6.65 mmol, 95%) as a pale yellow oil.
92%	With Oxalyl bromide; In dichloromethane; at 20℃;Reflux;	General procedure: To 16 (0.6 g, 0.6 mmol) was added dichloromethane (5 mL) in a round-bottom flask. After 10 min, oxalyl chlorideor oxalyl bromide was added (0.6 mmol). The reaction mixture was magnetically stirred at room temperature. Uponcessation of gas evolution, 4 was added (0.5 mmol), and the reaction mixture was heated to reflux. After thereaction was complete according to TLC analysis, the mixture was cooled to room temperature and filtered. Thesolid on the funnel was washed with dichloromethane (3 × 10 mL), and the filtrate was concentrated under reducedpressure to afford the desired product 5 in an essentially pure state based on 1H and 13C NMR spectroscopicanalyses.

88%	With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; ethyl acetate; Petroleum ether;	step 3 (3,3"-Dichloro-5'-[-(4-phenyl-butoxymethyl)-cyclopropylmethyl]-carbamoyl}-[1,1';3'1"]terphenyl-2'-yloxy)-methyl methyl ether To a solution of 4-phenyl-1-butanol (5.00 g, 33.3 mmol) and CH2Cl2 (250 mL) 15 at 0 C. was added triphenylphosphine (13.1 g, 50.0 mmol) followed by NBS (8.90 g, 50.0 mmol). After stirring at this temperature for 2 h, the mixture was quenched with H2O (50 mL) and extracted with CH2Cl2 (150 mL) The organic layer was washed with brine (40 mL) and dried (Na2SO4). After concentration, the residue was flushed through two quick columns of silica gel using 2% EtOAc/petroleum ether as an eluant to afford 4-phenylbutyl bromide (6.22 g, 88%) as an intermediate.
	With sulfuric acid; hydrogen bromide;	EXAMPLE 1 Manufacturing of 1-[4-(4-phenylbutoxy)phenyl]imidazole STR21 To 1.0 g of 4-phenyl-1-butanol, were added 0.33 g of concentrated sulfuric acid and 1.7 g of 47% aqueous solution of hydrobromic acid, and the resultant solution was then stirred for 5 hours at a temperature of from 140 to 150 C. while applying heating. The solution reacted was then poured into ice water and extracted with ethyl acetate. The organic layer resulted was dried with anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduced pressure, thereby affording 1.25 g of 4-phenyl-1-bromobutane.
	With sulfuric acid; hydrogen bromide;	EXAMPLE 6 Manufacturing of 1-[4-(4-phenylbutyloxy)benzyl]imidazole STR26 To 3.2 g of 4-phenyl-1-butanol, were added 1.0 g of concentrated sulfuric acid and 5.5 g of 47% aqueous solution of hydrobromic acid, and the resultant solution was stirred for 5 hours at 140-150 C. while applying heating. After completed the reaction, the solution was then poured into ice-water and extracted with ethyl acetate. The organic layer resulted was dried with anhydrous magnesium sulfate, and the solvent used was distillated under reduced pressure, thereby affording 2.7 g of 4-phenyl-1-bromobutane.
	With phosphorus tribromide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethyl acetate;	REFERENCE EXAMPLE 23 N,N-dimethyl-4-phenylbutylamine To 1.50 g of 4-phenylbutanol was added 385 mul of phosphorus tribromide with ice cooling, and the mixture was stirred at a room temperature for 5 minutes and then at 80 C. for one hour. To the reaction mixture were added 20 ml of ice water and 30 ml of ethyl acetate. The separated organic layer was, successively washed with water, 5% sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure to obtain an oily residue. The residue was applied to a silica gel column and eluted with hexane/benzene (6:1) to obtain 1.94 g of (4-bromobutyl)benzene as a colorless liquid.

Reference： [1]Patent: CN108911948,2018,A .Location in patent: Paragraph 0008; 0019; 0020; 0029
[2]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 4189 - 4192
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368
[4]Patent: WO2008/150492,2008,A1 .Location in patent: Page/Page column 84
[5]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 1397 - 1405
[6]Organic Letters,2018,vol. 20,p. 3061 - 3064
[7]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 335 - 341
[8]Patent: US6214877,2001,B1
[9]Tetrahedron Letters,2000,vol. 41,p. 3011 - 3014
[10]Journal of the Chemical Society. Perkin transactions I,1984,p. 195 - 198
[11]Tetrahedron,1987,vol. 43,p. 2543 - 2548
[12]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 1648 - 1655
[13]RSC Advances,2015,vol. 5,p. 63215 - 63225
[14]Organic and Biomolecular Chemistry,2014,vol. 12,p. 7612 - 7628
[15]European Journal of Organic Chemistry,2018,vol. 2018,p. 2277 - 2289
[16]Chemische Berichte,1982,vol. 115,p. 540 - 577
[17]Journal of the American Chemical Society,2009,vol. 131,p. 6475 - 6479
[18]Journal of the American Chemical Society,2015,vol. 137,p. 3731 - 3734
[19]Journal of Medicinal Chemistry,1981,vol. 24,p. 678 - 683
[20]Chemical Research in Toxicology,1997,vol. 10,p. 91 - 102
[21]Angewandte Chemie - International Edition,2006,vol. 45,p. 83 - 86
[22]Journal of the American Chemical Society,1953,vol. 75,p. 5037
[23],1936,vol. 6,p. 71
Chem.Abstr.,1941,p. 2120
[24]Chemische Berichte,1911,vol. 44,p. 2872
[25]Journal of the Chemical Society,1923,vol. 123,p. 2510
[26]Journal of the American Chemical Society,1963,vol. 85,p. 1597 - 1601
[27]Journal of Medicinal Chemistry,1963,vol. 6,p. 107 - 111
[28]Journal of Medicinal Chemistry,1965,vol. 8,p. 684 - 691
[29]Journal of the American Chemical Society,1964,vol. 86,p. 2687 - 2693
[30]Journal of Organic Chemistry,1971,vol. 36,p. 1620 - 1626
[31]Journal of Medicinal Chemistry,2002,vol. 45,p. 3549 - 3557
[32]Organic Letters,2002,vol. 4,p. 3793 - 3796
[33]Patent: US5965743,1999,A
[34]Patent: US5965743,1999,A
[35]Patent: US5093370,1992,A

2
[ 25077-25-2 ]
[ 13633-25-5 ]
3-(4-phenylbutyl)-1-methylglutarimide [ No CAS ]

Reference： [1]Heterocycles,1993,vol. 36,p. 71 - 78

3
[ 67686-01-5 ]
[ 13633-25-5 ]
1-Benzyl-4-(4-phenyl-butoxymethyl)-piperidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4344 - 4361

4
[ 13633-25-5 ]
[ 75-78-5 ]
[ 32328-67-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With magnesium In diethyl ether Heating;

Reference： [1]Maercker, Adalbert; Stoetzel, Reinhard [Journal of Organometallic Chemistry, 1984, vol. 269, # 3, p. C40 - C46]

5
[ 20315-68-8 ]
[ 13633-25-5 ]
[ 240117-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In acetonitrile

Reference： [1]Tamiz, Amir P.; Whittemore, Edward R.; Woodward, Richard M.; Upasani, Ravindra B.; Keana, John F.W. [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 11, p. 1619 - 1624]

6
[ 13633-25-5 ]
[ 105-53-3 ]
[ 78573-23-6 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 911 - 918
[2]Journal of Medicinal Chemistry,1999,vol. 42,p. 2610 - 2620
[3]Journal of Medicinal Chemistry,2002,vol. 45,p. 3639 - 3648

7
[ 13633-25-5 ]
[ 66943-05-3 ]
N-(4-phenylbutyl)-aza-15-crown-5 [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 2063 - 2066

8
[ 13633-25-5 ]
[ 64318-28-1 ]
[ 788825-02-5 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1101 - 1112

9
[ 13633-25-5 ]
[ 2365-48-2 ]
[ 945414-38-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In dimethyl sulfoxide; acetone; at 25℃; for 30h;	A solution of l-phenyl-4- bromobutane (1.30 g, 6.13 mmol) in a mixture of acetone/DMSO (4/1, 20 mL) was treated with K2CO3 (2.57 g, 18.6 mmol) and methyl thioglycolate (0.66 mL, 7.4 mmol). After stirring for 30 h at 25 C, the reaction mixture was quenched with an aqueous 1 N HCl solution and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. Column chromatography (SiO2, 4 x 10 cm, 25% EtOAc-hexanes) afforded S55 (1.31 g, 5.50 mmol, 90%) as a yellow oil: 1H NMR (CDCl3, 500 MHz) delta 7.37-7.34 (m, 2H), 7.28-7.24 (m, 3H), 3.81 (s, 3H), 3.29 (s, 2H), 2.70-2.75 (m, 4H), 1.85-1.69 (m, 4H).

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368
[2]Patent: WO2008/150492,2008,A1 .Location in patent: Page/Page column 84
[3]European Journal of Organic Chemistry,2018,vol. 2018,p. 2277 - 2289

10
[ 13633-25-5 ]
[ 128538-44-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 1-Bromo-4-phenylbutane With thiourea In ethanol for 4h; Inert atmosphere; Reflux; Stage #2: With sodium hydroxide In water for 2h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: ethanol / 24 h / Heating 2: NaOH / ethanol / 2 h / Heating
	Multi-step reaction with 2 steps 1: thiourea / ethanol 2: sodium hydroxide / water

Reference： [1]Fanourakis, Alexander; Paterson, Kieran J.; Phipps, Robert J.; Williams, Benjamin D. [Journal of the American Chemical Society, 2021, vol. 143, # 27, p. 10070 - 10076]
[2]Hamilton, Gregory S.; Wu, Yong-Qian; Limburg, David C.; Wilkinson, Douglas E.; Vaal, Mark J.; Li, Jia-He; Thomas, Christine; Huang, Wei; Sauer, Hansjorg; Ross, Douglas T.; Soni, Raj; Chen, Yi; Guo, Hongshi; Howorth, Pamela; Valentine, Heather; Liang, Shi; Spicer, Dawn; Fuller, Mike; Steiner, Joseph P. [Journal of Medicinal Chemistry, 2002, vol. 45, # 16, p. 3549 - 3557]
[3]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US5633379, 1997, A

11
[ 10041-02-8 ]
[ 13633-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH In N,N-dimethyl-formamide	1 Manufacturing of 1-[4-(4-phenylbutoxy)phenyl]imidazole STR21 0.5 g of 4-(imidazole-1-yl)phenol were added to 20 ml of DMF, and 0.14 g of 60% NaH were subsequently added thereto while cooling the solution with ice. After stirring the solution for 1 hour at room temperature, 0.73 g of 1-phenyl-4-bromobutane obtained hereinabove was fed dropwise to the solution while cooling it with ice.

Reference： [1]Current Patent Assignee: NIPPON SODA COMPANY LIMITED - US5965743, 1999, A

12
[ 106-41-2 ]
[ 13633-25-5 ]
1-bromo-4-(4-phenylbutoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.3%	With potassium carbonate; In N,N-dimethyl-formamide; for 2h;Reflux;	4-bromophenol (8.6 g, 49.9 mmol), 4-phenylbutyl bromide (11.2 g, 52.6 mmol) and potassium carbonate (13.7 g, (40 ml) was added under stirring with N, N-dimethylformamide (40 ml). The reaction was heated to reflux and refluxed at reflux conditions The reaction was carried out for 2 hours. The reaction solution was cooled to room temperature, water (160 ml) was added, and the mixture was extracted with ether (100 ml x 2) to combine the organic phases. The organic phase was washed successively with 0.5 M sodium hydroxide solution (110 ml) and water (110 ml), dried over anhydrous sodium sulfate and filtered to remove The filtrate was concentrated under reduced pressure and the concentrate was purified by silica gel chromatography to give 11.3 g of the title compound in 74.3% yield.
71%	With potassium carbonate; In N-methyl-acetamide;	EXAMPLE 1 Preparation of 4-(4-Phenylbutoxy)bromobenzene Potassium carbonate (7.6 g, 55.1 mmole), 4-bromophenol (5 g, 28.9 mmole) and 4-phenylbutylbromide (5.7 g, 26.8 mmole) were stirred in dimethylformamide (30 ml) and heated at 100 C. for two hours. The reaction mixture was quenched into water (150 ml) and the aqueous phase extracted with ether (2*75 ml). The combined ethereal extracts was washed with sodium hydroxide solution (~0.5 M, 120 ml) and water (100 ml). The organic layer was dried over sodium sulphate, filtered, and concentrated in vacuo to an oil. The crude product was purified using column chromatography (Stationary phase: silica; Eluent: petroleum ether (60/80) and then 9:1 (v/v) petroleum ether (60/80): dichloromethane) to give 4-(4-phenylbutoxy)bromobenzene (5.78 g, 71%). NMR (CDCl3) ppm, 1.72-1.82, 4H, m; 2.11-2.67, 2H, m; 3.85-3.89, 2H, m; 6.71, 2H, d; 7.14, 5H, m; 7.31, 2H, d. MS (E.I.) m/z (%) 65 (18), 91 (100), 104 (15), 117 (10), 132 (17), 172 (16), 304 (3).

Reference： [1]Patent: CN107253903,2017,A .Location in patent: Paragraph 0103; 0104; 0105; 0106
[2]Patent: US6048983,2000,A

13
[ 197506-83-5 ]
[ 13633-25-5 ]
methyl 1-(4-phenylbutyl)-3-formylindole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium tert-butylate; In chloroform; N,N-dimethyl-formamide;	17C Methyl 1-(4-phenylbutyl)-3-formylindole-5-carboxylate A solution of <strong>[197506-83-5]methyl 3-formylindole-5-carboxylate</strong> (2.234 g, 11.0 mmol) and potassium tert-butoxide (1.259 g, 11.2 mmol) in dry N,N-dimethylformamide (50 ml) was added with 1-bromo-4-phenylbutane (2.385 g, 11.2 mmol) and left under stirring at room temperature for 18 h. After that the solvent was evaporated off under reduced pressure, the resulting residue was partitioned between a NaCl saturated solution (50 ml) and chloroform (50 ml) and the aqueous phase was extracted with chloroform (3*50 ml). After drying and evaporating off the solvent under reduced pressure, a crude was obtained which was purified by chromatography through a silica gel column, eluding with n-hexane:ethyl acetate, 70:30, thereby obtaining 2.847 g of the title compound (87% yield). 1 H N.M.R. (300 MHz, CDCl3) delta ppm: 1.66 (m, 2H); 1.91 (m, 2H); 2.64 (t, 2H); 3.93 (s, 3H); 4.16 (t, 2H); 7.11 (d, 2H); 7.19 (m, 1H); 7.25 (d, 2H); 7.33 (d, 1H); 7.70 (s, 1H); 8.01 (dd, 1H); 8.99 (s, 1H); 9.98 (s, 1H).

Reference： [1]Patent: US5990142,1999,A

14
[ 524-38-9 ]
[ 13633-25-5 ]
[ 138504-80-0 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium iodide; potassium carbonate; In 1-methyl-pyrrolidin-2-one; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;	Method A 167.5 g (1.21 mol) of potassium carbonate and 2 g of potassium iodide were added to 302 g (1.85 mol) of N-hydroxyphthalimide in 1.9 l of anhydrous N-methylpyrrolidone. After the reaction mixture had been heated to 60 C., 395.2 g (1.85 mol) of 4-phenylbutyl bromide were added and this temperature was maintained for a further 6 hours. After cooling, the mixture was poured onto 6 l of ice water and taken up with dichloroethane, and the organic phase was washed with dilute sodium hydroxide solution, dried and evaporated down under reduced pressure. Yield: 379 g of N-(4-phenylbutoxy)-phthalimide (73%). 250-MHz 1 H-NMR (DMSO-d6) delta (ppm)=1.65-1.85 (m, 4H); 2.66 (t, 2H); 4.18 (t, 2H) 7.1-7.4 (m, 5H); 7.86 (s, 4H)

Reference： [1]Patent: US5364833,1994,A
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 3874 - 3883

15
[ 13633-25-5 ]
[ 105526-85-0 ]
(S)-1-(4-Phenylbutyl)-5-[(trityloxy)methyl]-2-pyrrolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In <i>N</i>-methyl-acetamide; acetone; paraffin oil	I (S)-1-(4-Phenylbutyl)-5-[(trityloxy)methyl]-2-pyrrolidinone Example I (S)-1-(4-Phenylbutyl)-5-[(trityloxy)methyl]-2-pyrrolidinone To 6 g of sodium hydride (55-60% dispersion in paraffin oil) in 50 ml of dry dimethylformamide, 40 g of (S)-5-[(trityloxy)methyl]-2-pyrrolidinone in 150 ml of dry dimethylformamide are added dropwise with stirring and cooling with ice. The mixture is then stirred for 2 hours at ambient temperature and then 32 g of 4-phenylbutylbromide in 50 ml of dry dimethylformamide are added dropwise. After 18 hours stirring at ambient temperature the mixture is poured onto ice, extracted three times with ethyl acetate, the combined organic phases are washed with water, dried over sodium sulphate and evaporated down. The crude product is purified over a silica gel column with toluene/acetone (4:1). Yield: 51.5 g (94% of theory), Rf value: 0.41 (silica gel; toluene/acetone=4:1)

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US5541343, 1996, A

16
[ 558-13-4 ]
[ 3360-41-6 ]
[ 13633-25-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triphenylphosphine; In dichloromethane; hexane-diethyl ether;	EXAMPLE 118 1-bromo-4-phenylbutane STR115 15.0 g (0.1 mol) 4-phenylbutanol and 39.8 g (0.12 mol) carbontetrabromide were dissolved in 500 ml dry dichloromethane and cooled to 0 C., 36.7 g (0.14 mol) triphenylphosphine was then added and the mixture stirred 1.5 hours under argon at 0 C. then evaporated in vacuo. The resulting mixture was stirred in ether-hexane (1:1) and filtered to remove insoluble material. The filtrate was then passed through a pad of silica gel and concentrated to give a pale yellow liquid 21.3 g. Yield: 100% of theory TLC Rf: 0.57 (ether-hexane 1:1). NMR (CDCl3, 60 MHz): 1.6-1.8[4]m, 2.55[2] t, J=7 Hz 3.3[2], t, J=7 Hz, 7.2[5]s.

Reference： [1]Patent: US5041638,1991,A

17
[ 2976-75-2 ]
[ 13633-25-5 ]
[ 103632-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane	R.15 (+-)-2-(1-Naphthoxy)-6-phenylhexanoic acid REFERENCE EXAMPLE 15 (+-)-2-(1-Naphthoxy)-6-phenylhexanoic acid To a mixture of 5 ml of dry tetrahydrofuran and 0.26 g of 50% sodium hydride (suspension in oil) were added 0.7 ml of diisopropylamine and 1.0 g of 1-naphthoxyacetic acid with stirring under an argon atmosphere under ice-cooling. The mixture was heated for 30 minutes at 50° C., and then heated under reflux for 15 minutes. After cooling below 5° C., to the reaction mixture was added dropwise 3.5 ml of n-butyllithium (as a 1.6 mole hexane solution), the mixture was stirred below 10° C. for 20 minutes, and then warmed for 20 minutes at 30° C. After cooling below 5° C. again, 1.00 g of 4-phenylbutyl bromide was added to the reaction mixture. The mixture was stirred for 30 minutes at below 5° C., and then warmed for 1 hour at 30° C. with stirring. After cooling, the reaction mixture was washed with diethyl ether to remove neutral materials. The aqueous layer was acidified by adding concentrated hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene) to obtain 0.37 g of (+-)-2-(1-naphthoxy)-6-phenylhexanoic acid as colorless crystals. Melting point: 91°-94° C. IR (KBr): νco 1700 cm-1. NMR (CDCl3) δ: 1.6-1.8(m, 4H), 2.05-2.2(m, 2H), 2.64(t, 2H, J=7.1 Hz), 4.8-4.9(m, 1H), 6.7-8.3(m, 12H).

Reference： [1]Current Patent Assignee: KISSEI PHARMACEUTICAL COMPANY LIMITED - US4863904, 1989, A

18
[ 13633-25-5 ]
[ 75937-12-1 ]
[ 928118-30-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In water; at 20℃; for 20h;	A solution of 4-phenylbutyl bromide (0.98 g, 4.6 mmol) and 44A (1.0 g, 4.6 mmol) in 10 mL of benzene was treated sequentially with Bu4NHSO4 (0.16 g, 0.46 mmol) and 50% aqueous NaOH (2.4 mL, 46 mmol, added slowly). After stirring at RT under N2 for 20 h, the solvent was removed. The reaction mixture was then diluted with H2O, extracted with EtOAc, washed with H2O (3×) and brine, dried over Na2SO4, and filtered. The filtrate was concentrated and chromatographed (5-10% EtOAc/hexanes) to provide 44B (0.7 g, 44%).

Reference： [1]Patent: US2007/93477,2007,A1 .Location in patent: Page/Page column 46-47

19
[ 13633-25-5 ]
[ 101-18-8 ]
[ 944284-94-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium hydroxide; In ethanol; for 5h;Heating / reflux;	lambda/-{2-r(3-phenylbutoxyphenylVphenyl- aminolethvDacetamide (5i): A mixture of lambda/-(3-hydroxyphenyl)aniline (2.7 mmol) and 1-bromo-4-phenylbutane (2.02 mmol) was refluxed for 5 h in a 10% ethanol solution of KOH. The reaction mixture was cooled to room temperature, poured into water and extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated under reduced pressure to provide a residue which was purified by flash chromatography (silica gel; cyclohexane/EtOAc, 8:2 as eluent). Yield lambda/-(3-phenylbutoxyphenyl)-aniline (3i): 86%; oil; EI-MS 317 (M+), 91 (100); 1H-NMR (CDCI3): delta 1.83 (m, 4H), 2.68 (m, <n="35"/>2H), 3.96 (m, 2H), 5.75 (br, 1 H), 6.46-7.38 (m, 14H).

Reference： [1]Patent: WO2007/79593,2007,A1 .Location in patent: Page/Page column 33-34

20
[ 13633-25-5 ]
[ 20872-28-0 ]
[ 691903-96-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20 - 50℃; for 3h;	Reference Example 37 ethyl [4-(4-phenylbutoxy)phenoxy]acetate A solution of ethyl (4-hydroxyphenoxy)acetate (0.49 g, 2.5 mmol), 4-phenylbutyl bromide (0.59 g, 2.8 mmol), potassium carbonate (0.69 g, 5.0 mmol) and potassium iodide (30 mg, 0.50 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 30 min., and further at 50C for 3 hrs. The solvent was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and saturated brine. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to give the title compound (0.62 g, yield 76%). oil. 1H NMR (CDCl3) delta 1.30 (3H, t, J=7.1 Hz), 1.78-1.83 (4H, m), 2.66-2.71 (2H, m), 3.90-3.94 (2H, m), 4.26 (2H, q, J=7.1 Hz), 4.56 (2H, s), 6.79-6.87 (4H, m), 7.18-7.21 (3H, m), 7.27-7.31 (2H, m).

Reference： [1]Patent: EP1559422,2005,A1 .Location in patent: Page/Page column 75; 76

21
[ 13633-25-5 ]
[ 4179-19-5 ]
[ 1017962-14-9 ]

Yield	Reaction Conditions	Operation in experiment
81%		3,5-Dimethoxytoluene (2.93 ml_, 20 mmol) and 4-phenylbutylbromide (4.13 ml_, 1.2 mmol) were reacted as described under General Procedure H and the crude product was purified by flash chromatography (silica-gel, petroleum ether/EtOAc 200:1) to afford the product as a clear oil (4.6 g, 81%). 1H NMR (300 MHz, CDCI3) delta 7.13-7.22 (m, 5H), 6.34 (s, 2H), 3.76 (s, 6H), 2.60-2.64 (m, 4H), 2.31 (s, 3H), 1.53-1.67 (m, 4H).; General Procedure H: Alkylation of <strong>[4179-19-5]3,5-dimethoxytoluene</strong> A solution of n-butyllithium in hexanes (1.7 M, 1.2 eq.) was added over 0.25 h to a solution of <strong>[4179-19-5]3,5-dimethoxytoluene</strong> (1.0 eq.) in THF (1 M) at 0 0C. The reaction mixture was stirred at 0 0C for 1 h then at room temperature for 3 h. The reaction was cooled to 0 0C and a solution of the alkyl bromide (1.2 eq.) in toluene (2 M) was added over 0.1 h. The reaction mixture was allowed to warm to room temperature and heated to 80 0C for 3-4 h. The reaction was quenched slowly with water and partitioned over EtOAc and water. The phases were separated and the <n="47"/>aqueous phase was extracted twice with EtOAc. The pooled organics were washed with brine, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography.
81%		68a) 1,3-Dimethoxy-5-methyl-2-(4-phenylbutyl)benzene; :A solution of nBuLi in hexanes (1.7 M, 14 ml_, 24 mmol) was added over 15 min to a solution of <strong>[4179-19-5]3,5-dimethoxytoluene</strong> (2.93 ml_, 20 mmol) in THF (20 mL) at 0 0C. <n="115"/>The reaction mixture was stirred at 0 C for 1 h then at room temperature for 3 h. The reaction was cooled to 0 0C and a solution of the 4-phenylbutylbromide (4.13 ml_, 1.2 mmol) in toluene (15 mL) was added over 5 min. The reaction mixture was allowed to warm to room temperature and heated to 80 0C for 3-4 h. The reaction was quenched slowly with water and partitioned over Et2theta (100 mL) and water (100 mL). The phases were separated and the aqueous phase was extracted with Et2O (3 x 100 mL). The pooled organics were washed with brine (120 mL), dried over Na2SO4, and concentrated under vacuum and the crude product was purified by flash chromatography (silica-gel, petroleum ether / EtOAc 200:1) to afford the product as a clear oil (4.6 g, 81 %). 1H NMR (CDCI3): delta 1.53-1.67 (m, 4H), 2.31 (s, 3H), 2.60-2.64 (m, 4H), 3.76 (s, 6H), 6.34 (s, 2H), 7.13-7.22 (m, 5H)1.

Reference： [1]Patent: WO2009/43117,2009,A1 .Location in patent: Page/Page column 45-46; 74
[2]Patent: WO2008/40057,2008,A1 .Location in patent: Page/Page column 113-114

22
[ 1489-97-0 ]
[ 13633-25-5 ]
[ 1189795-87-6 ]

Yield	Reaction Conditions	Operation in experiment
76%		b) 8-(4-phenylbutyl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester A 2.5 M solution of n-butyl lithium (2.5 g, 15.7 mL, 39.2 mmol) was slowly added in drops to a solution of diisopropylamine (3.96 g, 5.50 mL, 39.2 mmol) in absolute tetrahydrofuran (50 mL) at -78 C. in argon. 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidone (DMPU, 10.0 g, 9.42 mL, 78.2 mmol) and a solution of the title compound of the previous step (8.40 g, 39.2 mmol) in absolute tetrahydrofuran (30 mL) were added in drops one after the other to this mixture. The reaction solution was further stirred for 2 h at this temperature before a solution of 1-bromo-4-phenylbutane (10.0 g, 47.0 mmol) in absolute tetrahydrofuran (50 mL) was added in drops. The resulting solution was stirred overnight at room temperature. Saturated ammonium chloride solution (50 mL) was then added and extracted with ether (250 mL). The combined organic phases were washed with saturated sodium chloride solution (50 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (17.7 g) was purified by means of flash chromatography (400 g, 207.5 cm) with cyclohexane/ethyl acetate (9:1). Yield: 10.3 g (76%), colourless oil 1H-NMR (DMSO-d6): 1.12 (t, 3H, J=7.1 Hz); 1.39-1.62 (m, 12H); 1.91-2.03 (m, 2H); 2.54 (t, 2H, J=7.4 Hz); 3.82 (s, 4H); 4.05 (q, 2H, J=7.1 Hz); 7.12-7.17 (m, 3H); 7.22-7.28 (m, 2H).

Reference： [1]Patent: US2009/247530,2009,A1 .Location in patent: Page/Page column 31

23
[ 934753-05-6 ]
[ 13633-25-5 ]
[ 934738-10-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In acetonitrile; for 12h;Reflux;	Example 42A; Methyl 4-{(3E)-2-[2-(4-cyanophenyl)ethyl]-4-[2-(4-phenylbutoxy)phenyl]but-3-en-1-yl}benzoate A solution of 200 mg (0.486 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 5 ml of acetonitrile is mixed with 155 mg (0.73 mmol) of (4-bromobutyl)benzene and 100.76 mg (0.73 mmol) of potassium carbonate and then stirred under reflux for 12 h. After cooling, the potassium carbonate is filtered off and the filtrate is evaporated. 308 mg (0.41 mmol, 85% of theory, content 73%) of the title compound are obtained.LC-MS (method 2): Rt=3.38 min; MS (ESIpos): m/z=544 (M+H)+.

Reference： [1]Patent: US2010/29772,2010,A1 .Location in patent: Page/Page column 26

24
[ 1229444-44-3 ]
[ CAS Unavailable ]
[ 1229444-42-1 ]
[ 13633-25-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With carbon tetrabromide In 1,2-dichloro-ethane at 40℃; for 2h;

Reference： [1]Location in patent: scheme or table Imura, Yumi; Shimojuh, Naoya; Kawano, Yuhta; Togo, Hideo [Tetrahedron, 2010, vol. 66, # 19, p. 3421 - 3426]

25
[ 3240-34-4 ]
[ 13633-25-5 ]
[ 361979-96-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With p-nitrobenzenesulfonamide; iodine; In 1,2-dichloro-ethane; at 60℃; for 2h;Inert atmosphere;	General procedure: (Diacetoxyiodo)benzene (5 mmol, 1.61 g), I2 (0.4 mmol, 102 mg), p-toluenesulfonamide (0.4 mmol, 68.4 mg), and ethylbenzene (2 mmol, 184 mg) were added to dichloroethane (3 mL). The mixture was warmed at 60 C for 2 h under an argon atmosphere. Then, the mixture was poured into saturated aqueous sodium sulfite solution and extracted with diethyl ether (3 × 20 mL). The organic layer was dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the residue was subjected to preparative TLC on silica gel using a mixture of hexane and ethyl acetate (5:1) as an eluent to give alpha-(acetoxy)ethylbenzene in 63% yield.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4303 - 4307

26
[ 1821-12-1 ]
[ 13633-25-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4842 - 4845,4
[2]Synthesis,2013,vol. 45,p. 3233 - 3238
[3]Organic and Biomolecular Chemistry,2014,vol. 12,p. 7612 - 7628
[4]European Journal of Organic Chemistry,2018,vol. 2018,p. 2277 - 2289

27
[ 494199-22-3 ]
[ 13633-25-5 ]
[ 1433190-42-1 ]

Yield	Reaction Conditions	Operation in experiment
49%		General procedure: A solution of 4 in dry THF was stirred under argon at -20 C. A solution of n-butyllithium, 2.5 M in hexane (1.5 equiv), was added to the reaction, producing a deep red color. The mixture was stirred at -20 C for 2 h. Alkyl bromide (1.5 equiv) was added, producing a yellow solution, which was then stirred and brought to 20 C over 1 h. The reaction mixture was then treated with saturated NH4Cl solution. The reaction mixture was partitioned between Et2O and H2O. The organic layer was dried over anhyd Na2SO4 and removal of the solvent gave an orange oil. Column chromatography of the crude material using 20% hexanes in Et2O gave compound 5 as a pure yellow oil.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3298 - 3309
[2]European Journal of Medicinal Chemistry,2015,vol. 92,p. 531 - 539

28
[ 454-31-9 ]
[ 13633-25-5 ]
[ 127119-00-0 ]

Yield	Reaction Conditions	Operation in experiment
45%		General procedure: To a stirring mixture of magnesium (24mg, 1mmol) and iodine in dry Et2O (1mL), a solution of bromide 14a or 14b (1mmol) in dry Et2O (9mL) was added dropwise under N2 atmosphere. Once the Grignard reagent was formed, it was added dropwise to a cooled (-78C) solution of ethyl difluoroacetate (62mg, 0.5mmol) in dry ether (0.5mL). The reaction mixture was stirred at -78C for 45min and then was quenched with 1N HCl. The aqueous layer was extracted with ether (3×25mL) and the combined organic layers were washed with brine, dried (Na2SO4) and the solvent was evaporated in vacuo. The product was purified by flash column chromatography [EtOAc-petroleum ether (bp 40-60C) 5/95].

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5823 - 5829

29
[ 6704-31-0 ]
[ 13633-25-5 ]
[ 1439367-59-5 ]

Yield	Reaction Conditions	Operation in experiment
35%		Under argon atmosphere at -45C, to a stirred mixture of Lithium in pellets (0.129g, 18.7 mmol) suspended in dry Et20 (15 mL), 4-bromo-butylbenzene (1.5 g, 7.03 mmol) in dry Et20 (10 mL), was added dropwise. The reaction was left to stir at 0C for 3h, then the mixture was transferred via a cannula to a solution of 3-oxetanone (0.4 g, 5.55 mmol) in dry THF (10 mL), previously cooled to -78C. After 3h at -78C, the reaction mixture was quenched with a saturated NH4C1 solution, the organic solvents removed under reduced pressure. The crude mixture was then dissolved in CH2C12, dried over Na2S04, concentrated to dryness and subjected to column chromatography using a Teledyne ISCO apparatus, eluting with Cy/TBME (from 100:0 to 70:30) to afford a pure compound (0.4 g, 35%) as colorless oil. '1HNMR (CDC13): delta 1.41-1.55 (m, 2H), 1.65-1.78 (m, 2H), 1.84-1.94 (m, 2H), 2.62-2.73 (m, 2H), 4.52 (d, J= 7.2 Hz, 2H), 4.58 (d, J= 7.0 Hz, 2H), 7.21 (dd, J= 5.4, 7.2 Hz, 3H), 7.27-7.34 (m, 2H).
35%		Step 1. Preparation of 3-(4-phenylbutyl)-oxetan-3-ol Under argon atmosphere at -45 C., to a stirred mixture of Lithium in pellets (0.129 g, 18.7 mmol) suspended in dry Et2O (15 mL), 4-bromo-butylbenzene (1.5 g, 7.03 mmol) in dry Et2O (10 mL), was added dropwise. The reaction was left to stir at 0 C. for 3 h, then the mixture was transferred via a cannula to a solution of 3-oxetanone (0.4 g, 5.55 mmol) in dry THF (10 mL), previously cooled to -78 C. After 3 h at -78 C., the reaction mixture was quenched with a saturated NH4Cl solution, the organic solvents removed under reduced pressure. The crude mixture was then dissolved in CH2Cl2, dried over Na2SO4, concentrated to dryness and subjected to column chromatography using a Teledyne ISCO apparatus, eluting with Cy/TBME (from 100:0 to 70:30) to afford a pure compound (0.4 g, 35%) as colorless oil. 1H NMR (CDCl3): delta 1.41-1.55 (m, 2H), 1.65-1.78 (m, 2H), 1.84-1.94 (m, 2H), 2.62-2.73 (m, 2H), 4.52 (d, J=7.2 Hz, 2H), 4.58 (d, J=7.0 Hz, 2H), 7.21 (dd, J=5.4, 7.2 Hz, 3H), 7.27-7.34 (m, 2H).

Reference： [1]Patent: WO2013/78430,2013,A1 .Location in patent: Paragraph 0290
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 10101 - 10111
[3]Patent: US9353075,2016,B2 .Location in patent: Page/Page column 102

30
[ 13633-25-5 ]
[ 10128-72-0 ]
[ 1461603-32-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	Intermediate 30: methyl 3-I(4-phenylbutyl)oxyl-4-pyridinecarboxylate To a solution of <strong>[10128-72-0]methyl 3-hydroxy-4-pyridinecarboxylate</strong> (100 mg, 0.65 mmol) in DMF (2 ml) wasadded cesium carbonate (426 mg, 1 .31 mmol) followed by (4-bromobutyl)benzene (139 mg, 0.65mmol). The mixture was allowed to stir at room temperature for 16 h then concentrated in vacuo. The crude product was dissolved in DMSO (1 ml) and purified by MDAP using a formic modifier (Method G). Fractions containing desired product were loaded directly onto a 5g SCX-ll SPE column that had been preconditioned with isopropylalcohol. The column was eluted with isopropylalcohol (3 x 50 ml)then with a 10% ammonia inwater/90% isopropylalcohol solution. Desired product eluted in ammonia based fractions which were combined then concentrated under reduced pressure to give the title compound as a pale brown gum (1 23mg, 66%).LCMS (Method B): Rt= 1.19 mins, MH+ = 286.1

Reference： [1]Patent: WO2013/143597,2013,A1 .Location in patent: Page/Page column 54

31
[ 30089-00-0 ]
[ 13633-25-5 ]
[ 123-01-3 ]

Yield	Reaction Conditions	Operation in experiment
84 mg	With [((Me)NN₂)NiCl]; isopropyl alcohol; sodium iodide; sodium hydroxide In 1,4-dioxane at 80℃; for 24h; Inert atmosphere;	Alkyl-Alkyl Coupling Reactions; General Procedure General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 mol%), NaI (37 mg, 0.25 mmol, 0.5 equiv), and i-PrOH (76 μL, 1 mmol, 2 equiv) in dry 1,4-dioxane (2.4 mL), were added alkyl halide (0.5 mmol) and the alkyl-(9-BBN) (1.6 mL, 0.8mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 °C for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 × 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product (Tables 1 and 2).

Reference： [1]Di Franco, Thomas; Boutin, Nicolas; Hu, Xile [Synthesis, 2013, vol. 45, # 21, p. 2949 - 2958]

32
[ 13633-25-5 ]
[ 98-80-6 ]
[ 1083-56-3 ]

Yield	Reaction Conditions	Operation in experiment
21%	With Bis<2-(N,N-dimethylamino)aethyl>aether; [((Me)NN2)NiCl]; sodium iodide; sodium hydroxide; In tert-Amyl alcohol; at 80℃; for 24h;Inert atmosphere;	General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 mol%), NaI (37 mg, 0.25 mmol, 0.5 equiv), and OTMEDA (241 mg, 1.5 mmol, 3 equiv) in dry EtCMe2OH (4 mL),were added alkyl halide (0.5 mmol) and the phenylboronic acid (98mg, 0.8 mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 C for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 × 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product( Tables 3 and 4).

Reference： [1]Synthesis,2013,vol. 45,p. 2949 - 2958

33
[ 13633-25-5 ]
[ 154848-44-9 ]
[ 1593090-71-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate at 20 - 40℃; Inert atmosphere;

Reference： [1]Ono, Katsuki; Takeuchi, Koh; Ueda, Hiroshi; Morita, Yasuhiro; Tanimura, Ryuji; Shimada, Ichio; Takahashi, Hideo [Angewandte Chemie - International Edition, 2014, vol. 53, # 10, p. 2597 - 2601]

34
[ 616-45-5 ]
[ 13633-25-5 ]
[ 1616591-75-3 ]

Yield	Reaction Conditions	Operation in experiment
91%		To a solution of pyrrolidin-2-one (3 mL; 40 mmol) in 80 mL of anhydrous toluene, was added NaH (0.95 g, 40 mmol.) in 60% suspension in paraffin oil (1.58 g suspension). After stopping of hydrogen release, the reaction mixture was heated to reflux with stirring under nitrogen atmosphere for 10 h. Then omega-phenylalkylbromide (80 mmol) dissolved in anhydrous xylene (20 mL) was added. The mixture was then refluxed for 4 h under nitrogen atmosphere. After cooling and filtration, solvent was eliminated under reduced pressure. The viscous residue was purified by flash chromatography using CH2Cl2 / MeOH (99/1) to give compound 1c

Reference： [1]Synthetic Communications,2014,vol. 44,p. 2377 - 2385

35
[ 124-38-9 ]
[ 13633-25-5 ]
[ 2270-20-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With manganese; (1,2-dimethoxyethane)dichloronickel(II); 2,9-diethyl-1,10-phenanthroline In N,N-dimethyl acetamide at 20℃; for 12h; Schlenk technique;

Reference： [1]Liu, Yu; Cornella, Josep; Martin, Ruben [Journal of the American Chemical Society, 2014, vol. 136, # 32, p. 11212 - 11215]

36
[ 13633-25-5 ]
[ 2802-06-4 ]
[ 1333227-89-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In methanol; at 20℃;	General procedure: To a solution of iminodiacetic acid hydrochloride (2 mmol) in MeOH (10 mL) were added NEt3 (6 mmol) and the corresponding bromide derivative (2 mmol). The mixture was stirred overnight at room temperature. The crude product was purified by preparative HPLC.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 90,p. 547 - 567

37
[ 13633-25-5 ]
4a-(4-phenylbutyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]
2,4a-bis(4-phenylbutyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 50℃; for 20h;	General procedure: A mixture of the amine 9, alkyl bromide (1.2 equiv) and NaHCO3 (2 equiv) in DMF (20mL) was heated at 50C for 20h. After cooling to room temperature, the reaction mixture was poured into ice- H2O, and the product was extracted with Et2O. The ethereal extracts were washed with saturated NH4Cl solution, dried over Na2SO4, and the solvent was removed in vacuo to afford an oil. The crude oil was subjected to flash chromatography on silica gel using 75% EtOAc in hexanes as the eluent to give the 10-12 as solids.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 92,p. 531 - 539

38
[ 13633-25-5 ]
[ 1401938-80-4 ]
(3'R,5'S,8'R,9'S,10'S,13'S,14'S)-10',13'-dimethyl-4"-(4-phenylbutyl)tetradecahydro-2'H,6"H-dispiro[1,3-dioxolane-2,17'-cyclopenta[a]phenanthrene-3',2"-[1,4]oxazinan]-6"-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		General procedure: To a solution of 4a-4e (0.1 mmol) in dry DCM (5 mL) was addedDIPEA (0.17 mmol) in a Schlenk tube. The tube was screwed down,stirred and heated at 75 C for 10 min, and the reaction mixturewas cooled to room temperature and benzyl bromide (1.7 mmol)was added to the solution. The reaction mixture was stirred andheated at 75 C for 48 h. After cooling the mixture, silica gel wasadded to the crude mixture, the solvent was evaporated underreduced pressure and the residue was purified by flash chromatography with a mixture of hexanes/EtOAc/TEA (95:5:1).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5433 - 5451

39
[ 13633-25-5 ]
[ 123770-62-7 ]
ethyl 5-(4-phenylbutoxymethyl)isoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.65 g		Reference Production Example 107 (0749) 60% Sodium hydride (1.04 g, 26.0 mmol) was added to dehydrated N,N-dimethylformamide (10 ml) cooled to 0C, under a nitrogen atmosphere, and a dehydrated N,N-dimethylformamide (10 ml) solution of <strong>[123770-62-7]ethyl 5-hydroxymethylisoxazole-3-carboxylate</strong> (3.0 g, 17.54 mmol) was added dropwise thereto, and then the mixture was further stirred for 30 minutes. A dehydrated N,N-dimethylformamide (5 ml) solution of 1-bromo-4-phenylbutane (3.73 g, 17.54 mmol) was added thereto, and the mixture was heated to room temperature and stirred for 16 hours. Then, the mixture was added to a saturated aqueous ammonium chloride solution, and extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 1.65 g of ethyl 5-(4-phenylbutoxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 7.27 (m, 2H), 7. 17 (m, 3H), 6.65 (s, 1H), 4.60 (s, 2H), 4.45(q, 2H), 3.53(t, 2H), 2.63 (t, 2H), 1.68 (m, 4H), 1.46(t, 3H)

Reference： [1]Patent: EP2952096,2015,A1 .Location in patent: Paragraph 0749

40
[ 13633-25-5 ]
[ 26663-77-4 ]
methyl 1-(4-phenylbutyl)-1H-benzo[d]imidazole-5-carboxylate [ No CAS ]
C₁₉H₂₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; for 2h;	Compound 15 (0.5 g, 2.84 mmol) was reacted with 4-phenylbutylbromide (0.5 mL, 2.84 mmol) in anhydrous DMF(10 mL) and K2CO3 (0.79 g, 5.68 mmol) was added slowly at 0C.The resulting reaction mixture was warmed to 60C and stirredfor 2 h. After completion, reaction mixture was quenched withsaturated NH4Cl, and extracted with ethyl acetate (250 mL). Thecombined organic layers were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The crude residuewas purified over silica gel column chromatography (MeOH/DCM= 1:49) to yield the mixture of isomers 16 (0.79 g, 90%) as acolorless liquid.Spectral data for isomers. 1H NMR (CDCl3, 300 MHz); delta8.53 (s, 1H), 8.10 (t, 2H, J= 6.0 Hz), 7.34-7.29 (m, 3H), 7.16-7.14(m, 3H), 4.23-3.94 (m, 2H), 2.68-2.63 (m, 2H), 2.30-2.20 (m, 2H).13C NMR (CDCl3, 75 MHz): 167.7, 147.3, 144.6, 139.9, 133.4,128.7, 126.5, 124.8, 123.5, 122.8, 120.1, 112.1, 52.2, 44.5, 32.6,30.9.

Reference： [1]PLoS ONE,2014,vol. 9

41
[ 13633-25-5 ]
[ 26663-77-4 ]
1-(4-phenylbutyl)-1H-benzo[d]imidazole-5-carboxylic acid [ No CAS ]
C₁₈H₁₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4N HCl (10 mL) was added to compound 16 (0.7 g,2.27 mmol) in 1,4-dioxane (5 mL) and refluxed for 2 h. Thereaction mixture was concentrated under vacuum and dissolved inethyl acetate (20 mL). The mixture was washed with saturatedNaHCO3, brine and dried over anhydrous Na2SO4. Thecombined organic layer was concentrated under vacuum. Thecrude residue was purified using silica gel column chromatography(MeOH/DCM, from 1:20 to 1:5) to yield the mixture of isomers14a and14b (0.56 g, 84%) as liquid.Spectral data for isomers. 1H NMR (CDCl3, 300 MHz); delta8.51 (s, 1H), 8.12 (t, 2H, J= 6.0 Hz), 7.32-7.21 (m, 3H), 7.17-7.13(m, 3H), 4.21-3.93 (m, 2H), 2.65-2.61 (m, 2H), 2.32-2.23 (m, 2H).13C NMR (CDCl3, 75 MHz): 166.7, 147.1, 144.2, 138.3, 134.6,126.9, 125.6, 124.9, 123.5, 121.3, 111.1, 51.1, 45.8, 33.4, 29.6.

Reference： [1]PLoS ONE,2014,vol. 9

42
[ 13633-25-5 ]
[ 1004-39-3 ]
2-((4-phenylbutyl)thio)pyrimidine-4,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5.2%	With potassium iodide; potassium hydroxide; In ethanol; water; at 80℃; for 6h;	Compound 26-2 (100 mg, 0.70 mmol, 1.0 eq.) was dissolved in EtOH/H20 (10 mE/S mE), added KI (11.6 mg, 0.07 mmol, 0.1 eq.), and then, slowly added compound 25-1 (445 mg, 2.1 mmol, 3.0 eq.). The reaction was heated at 80 C. for 6 h, monitored by TEC. After the reaction was completed, the mixture was added dilute hydrochloric acid (1M, 10 mE), followed by extracted three times with ethyl acetate (15 mE). The combined organic extracts were washed with brine, dried, filtered, and concentrated. The residue was purified by a flash chromatography on silica gel (DCM:MeOH=30: 1) to give compound EY274-a (white solid, 10mg, 5.2%). ?H NMR (300 MHz, DMSO) oe 7.26 (m, 2H), 7.19 (m, 3H), 6.02 (s, 4H), 5.12 (s, 1H), 3.00 (t, J6.6 Hz, 2H), 2.59 (q, J6.6 Hz, 2H), 1.62 (m, 4H).

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 579 - 583
[2]Patent: US2018/237399,2018,A1 .Location in patent: Paragraph 0152; 0153

43
[ 13633-25-5 ]
[ 368-54-7 ]
2-((4-phenylbutyl)thio)-6-(trifluoromethyl)pyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.2%	With potassium iodide; potassium hydroxide; In ethanol; water; at 80℃; for 6h;	Compound 26-1 (100 mg, 0.50 mmol, 1.0 eq.) was dissolved in EtOH/H20 (10 mE/S mE), added KI (11.3 mg, 0.069 mmol, 0.1 eq.), and then, slowly added compound25-1 (318 mg, 1.50 mmol, 3.0 eq.). The reaction was heated at 80 C. for 6 h, monitored by TEC. After the reaction was completed, the mixture was added dilute hydrochloric acid (1M, 10 mE), followed by extracted three times with ethyl acetate (15 mE). The combined organic extracts were washed with brine, dried, filtered, and concentrated. The residue was purified by a flash chromatography on silica gel (DCM:MeOH=30: 1) to give compound EY328 (white solid, 80 mg, 67.2%). ?H NMR (300 MHz, DMSO) oe 13.50 (s, 1H), 7.32-7.22 (m, 2H), 7.17 (m, 3H), 6.58 (s, 1H), 3.16 (t, J=9.6 Hz, 2H), 2.60 (q, J=6.9 Hz, 2H), 1.67 (m, 4H)

Reference： [1]Patent: US2018/237399,2018,A1 .Location in patent: Paragraph 0155; 0157
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 579 - 583

44
[ 13633-25-5 ]
[ 24070-52-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With 4,5,6,7-tetrafluoro-2-hydroxy-3-(2,2,2-trifluoroethoxy)-3-trifluoromethylisoindolin-1-one; oxygen; cobalt(II) acetate; manganese(III) triacetate dihydrate; In 2,2,2-trifluoroethanol; at 60℃; under 760.051 Torr; for 48h;	General procedure: To a solution of benzoate 36a (72.1 mg, 0.300 mmol) in 35(5.8 mg, 0.015 mmol), TFE (0.15 mL), Co(OAc)2 (0.53 mg,0.00300 mmol) and Mn(OAc)3·H2O (0.80 mg, 0.00300 mmol)were added. The reaction mixture was stirred for 48 h at 60Cunder O2 atmosphere. The mixture was evaporated under reducedpressure, and the residue was purified with flash columnchromatography (SiO2, n-hexane-EtOAc=9 : 1) to afford ketone37a (59.8 mg, 75%).

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 737 - 753

45
[ 4424-20-8 ]
[ 13633-25-5 ]
C₂₀H₂₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux;

Reference： [1]Mbofana, Curren T.; Chong, Eugene; Lawniczak, James; Sanford, Melanie S. [Organic Letters, 2016, vol. 18, # 17, p. 4258 - 4261]

46
[ 4424-20-8 ]
[ 13633-25-5 ]
C₂₀H₂₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate; potassium iodide / acetonitrile / 18 h / Reflux 2.1: trifluoroacetic acid / 0.08 h / Sealed tube 2.2: 48 h / 20 °C

Reference： [1]Mbofana, Curren T.; Chong, Eugene; Lawniczak, James; Sanford, Melanie S. [Organic Letters, 2016, vol. 18, # 17, p. 4258 - 4261]

47
[ 13633-25-5 ]
[ 112626-50-3 ]
C₁₇H₂₅N [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4258 - 4261

48
[ 13633-25-5 ]
[ 112626-50-3 ]
C₁₇H₂₃NO [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4258 - 4261

49
[ 846589-98-8 ]
[ 13633-25-5 ]
[ 1983127-62-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; potassium iodide In acetonitrile at 90℃; for 18h; Sealed tube;

Reference： [1]Mbofana, Curren T.; Chong, Eugene; Lawniczak, James; Sanford, Melanie S. [Organic Letters, 2016, vol. 18, # 17, p. 4258 - 4261]

50
[ 13633-25-5 ]
[ 17337-13-2 ]
N-([1,1'-biphenyl]-2-yl)-5-phenylpentanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With manganese; 6,6'-dimethyl-2,2'-bipyridine; nickel dibromide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; chemoselective reaction;

Reference： [1]Serrano, Eloisa; Martin, Ruben [Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11207 - 11211][Angew. Chem., 2016, vol. 128, # 37, p. 11373 - 11377]

51
[ 13633-25-5 ]
[ 92136-39-5 ]
tert-butyl (4-phenylbutyl)(prop-2-yn-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		To a stirred solution of tert-Butylprop-2-yn-1-ylcarbamate (300 mg, 1.93 mmol, 1 eq.) in dry DMF (1.93 mL) under nitrogen at 0C, was added NaH (93 mg, 60% in oil, 2.32 mmol, 1.2 eq.) in small portions. After stirring for 15min, (4-bromobutyl)benzene (410 muL, 2.34 mmol, 1.2 eq.) was added dropwise followed by KI(32 mg, 0.19 mmol, 0.1 eq.) and the reaction was warmed up to room temperature for 15 h.After completion of the reaction, water and brine were added and the aqueous layer wasextracted with Et2O (three times). Then, the combined organic layers were dried over MgSO4,filtered and concentrated under vacuum. The crude residue was purified by flash columnchromatography on silica gel (cyclohexane/DCM: 50/50) to afford 1h (446 mg, 1.54 mmol, 80%)as a colorless oil. 1H NMR (300 MHz, CDCl3): delta 7.31-7.24 (m, 2H), 7.21-7.14 (m, 3H), 4.01 (br. s,2H), 3.33 (t, J = 6.6 Hz, 2H), 2.64 (t, J = 7.1 Hz, 2H), 2.16 (t, J = 2.4 Hz, 1H), 1.67-1.56 (m, 4H),1.45 (s, 9H); 13C NMR (100 MHz, CDCl3): delta 155.2 (br. s), 142.4 (br. s), 128.5 (2C), 128.4 (2C),125.8, 80.2, 80.0 (br. s), 71.4 (br. s), 46.4, 36.4 and 36.0 (br. S, rot.), 35.6, 28.6 (br. s), 28.5 (3C),27.6 (br. s).

Reference： [1]Synlett,2016,vol. 27,p. 2575 - 2580

52
[ 867-13-0 ]
[ 13633-25-5 ]
diethyl (1-ethoxycarbonyl-2-phenylpentyl)phosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		General procedure: A solution of ethyl-2-(diethoxyphosphoryl) acetate 5 in DMF(25 mL/mol) was stirred at 0 C. The base was added and the solutionwas continued to stir for 20 min before the alkyl halide wasadded drop wise. The reaction mixture was allowed to warm toroom temperature and then heated at 60 C for 18 h. After coolingthe reaction mixture was acidified with 10% citric acid andextracted with diethyl ether (3 x 30 mL). The combined organicphases were washed with H2O (3 x 30 mL), brine (1 30 mL) anddried over Na2SO4. The product 6a-c was purified with columnchromatography using 2:1 diethyl ether/pentane as eluent.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 135,p. 159 - 173

53
[ 13633-25-5 ]
[ 171800-72-9 ]
[ 1208109-89-0 ]

Yield	Reaction Conditions	Operation in experiment
66%		A mixture of 8d hydrochloride (0.15 g, 0.53 mmol), N-ethyldiisopropylamine(0.34 g, 2.7 mmol) and sodium hydride (0.07 g,1.8 mmol) in DMF (5 mL) was stirred for 0.5 h at rt. To the mixturewas added 4-phenylbutylbromide (0.50 g, 2.35 mmol) in an icebath,and the mixture was stirred for 2 h at 120 C. The mixturewas partitioned between ethyl acetate and water, and the aqueouslayer was extracted with ethyl acetate. The combined organic layerwas washed with brine, dried (Na2SO4) and concentrated in vacuo.The residue was purified by column chromatography on basic silicagel (n-hexane/EtOAc = 15/1-10/1) to produce pale brown oils, to asolution of which in ether (5 mL) was added 4 N HCl/EtOAc(0.15 mL, 0.6 mmol) dropwise in an ice-bath, and the precipitatewas filtered off to obtain 3g (0.15 g, 66%) as pale brown crystals.1H NMR (DMSO-d6) d 1.40-2.73 (14H, m), 2.80-3.40 (6H, m),3.87 (3H, s), 6.99-7.03 (2H, m), 7.16-7.32 (5H, m), 7.97 (1H, d,J = 8.4 Hz), 9.45 (1H, brs); Anal. Calcd for C25H32NO2ClHCl0.5H2O:C, 70.99; H, 7.86; N, 3.31. Found: C, 71.75; H, 8.26; N, 3.32; LC/MS(ESI) m/z 378 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3719 - 3735

54
[ 13633-25-5 ]
1-(2'-pyridyl)-9H-pyrido<3,4-b>indole [ No CAS ]
1-(2-pyridyl)-9-(4-phenylbutyl)-β-carboline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydride; In N,N-dimethyl-formamide;	3) 0.24 g (10 mmol) of sodium hydride and 15 ml of N, N-dimethylformamide were added to a 50 ml round bottom flask at room temperatureStir for 10 minutes,Then, 2.5 g (10 mmol) of compound 2 and 10 mmol of 1-bromo-4-phenylbutane were added and subjected to thin layer chromatography to the end of the reaction. The reaction solution was then poured into 500 ml of ice water, extracted three times with 100 ml of ethyl acetate,The organic phase was combined and the solvent was evaporated to dryness. The resulting residue was purified by silica gel column chromatography (V dichloromethane: V methanol = 100: 1) to give Compound 3 (3.1 g, yield 82%).
70%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 1h;	General procedure: To a stirred solution of 1-(2-pyridyl)-b-carboline (0.245 g,1 mmol) in 10 mL DMF, sodium hydride (50% in mineral oil, 0.048 g,1 mmol) and bromo-hydrocarbon (1 mmol) was added. The reactionmixturewas stirred at room temperature for 1 h. After reactionwas finished, the mixture was poured into ice water and extractedwith ethyl acetate. The organic layer was washed with water anddried. Removal of the solvent gave the crude product that waspurified by silica gel column (dichloromethane: methanol 100:1 as the eluent). The solvent was removed and the product wasobtained.

Reference： [1]Patent: CN106478690,2017,A .Location in patent: Paragraph 0017; 0044; 0047
[2]European Journal of Medicinal Chemistry,2019,vol. 181

55
[ 13633-25-5 ]
[ 66-22-8 ]
[ 13345-76-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; sodium iodide; In dimethyl sulfoxide; at 90 - 120℃; for 17.5h;	General procedure: Method D: Into a mixture of uracil (2-3 equiv.), K2CO3 (2-3 equiv.), and NaI (1 equiv.) in DMSO (0.5-1 M) was added alkyl bromide (1 equiv.). The mixture was stirred and heated at 90 C, then cooled to room temperature. Water (20 mL) was added and the mixture was acidified to pH 2 using 4 M HCl. Unless otherwise mentioned, all products were collected via trituration using EtOAc/hexanes and/or EtOH/hexanes upon filtration.

Reference： [1]Patent: WO2017/161119,2017,A1 .Location in patent: Page/Page column 172; 185

56
[ 13633-25-5 ]
[ 144649-99-0 ]
2-methoxy-5-(1-phenylbutyl)benzonitrile [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 13929 - 13935

57
[ 13633-25-5 ]
[ 30131-16-9 ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679
[2]ChemMedChem,2018,vol. 13,p. 2530 - 2545

58
[ 13633-25-5 ]
[ 99-76-3 ]
[ 136450-05-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrabutyl-ammonium chloride; potassium carbonate; In water; at 90℃; for 15h;	Add 350mL of water to a 1L four-neck bottle,94.7g (1.05eq) of methyl paraben,114.5g (1.4eq) of potassium carbonate,Tetrabutylammonium chloride 3g (3%),1-bromophenylbutane 94.6g (1eq),Heated to 90 C for 15h,The area of the raw material (1-bromophenylbutane) monitored by HPLC was normalized to less than 1%.Reduce the temperature to 60 C and add 700mL of water. Layer while hot at 60 C. Keep the upper organic layer and separate the water layer.To give methyl p-butoxybutyrate,The yield was 90%.

Reference： [1]Patent: CN110357772,2019,A .Location in patent: Paragraph 0084; 0087
[2]New Journal of Chemistry,2017,vol. 41,p. 4672 - 4679
[3]ChemMedChem,2018,vol. 13,p. 2530 - 2545

59
[ 101-55-3 ]
[ 13633-25-5 ]
C₂₂H₂₂O [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 310 - 313

60
[ 13633-25-5 ]
[ 99-76-3 ]
[ 30131-16-9 ]

Yield	Reaction Conditions	Operation in experiment
98.7%		Step 1. In a 250 ml three-necked flask, 1 g of a catalyst P-W2CNC, 1-bromo-4-phenylbutane 8.0 g, DMF 50 ml, and mechanical stirring were sequentially added.Put 1.8 g of methylparaben, K2CO 33.6 g, and heat to 115 C.Reaction 11h;Step 2: After the reaction is cooled to room temperature, the K2CO3 solid is removed by suction filtration.Add 50 ml of water to the filtrate, turbid, stir for 10 min, add about 3 mol / L of HCl solution to adjust pH = 2;Step 3. Extract the above system with dichloromethane, wash with ionized water,The solvent dichloromethane was removed by rotary evaporation to give an orange liquid;Step 4, the orange liquid is placed in a single-mouth bottle, 3.0 g of NaOH, 50 ml of water and 40 ml of ethanol are added, and the mixture is refluxed for 3 hours in an oil bath, and the ethanol is distilled off.The residue was adjusted to pH=2 with 3 mol/L of HCl;Step 5, after extracting the above system with dichloromethane, the organic phase is steamed.A sticky yellow solid was obtained, and after adding an appropriate amount of isopropanol, the mixture was stirred, solid crystallized, and suction filtered to give white crystals of 4-(4-phenylbutoxy)benzoic acid.

Reference： [1]Patent: CN108689843,2018,A .Location in patent: Paragraph 0010-0031

61
[ 503-30-0 ]
[ 13633-25-5 ]
[ 94399-85-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With bis(acetylacetonate)nickel(II); (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium 2,2,2-trifluoroacetate; sodium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In benzene;Schlenk technique;	General procedure: General Procedure 3: An oven-dried 12.0 ml_ Schlenk tube containing a stirring bar was charged with the compound of formula (Ilia) (20 mol%, 16.8 mg, 0.06 mmol), L2 (10 mol%, 8.1 mg, 0.03 mmol), alkyl bromide (0.30 mmol, if solid), CF3C02Na (1.0 eq, 40.8 mg, 0.3 mmol). The schlenk tube was transferred to a nitrogen-filled glove-box where the Ni(acac)2 (10 mol%, 7.7 mg, 0.03 mmol), Na2C03 (1.0 eq, 32.0 mg, 0.30 mmol), alkyl bromide of formula R?-Br (0.30 mmol, if liquid) and anhydrous THF (0.075 M, 4ml_) were added. Then, the mixture was stirred for 1 minute and taken out of the glovebox. The Schlenk tube was placed approximately ~3 cm away from two 32 W CFL and it was rigorously stirred for 36- 96 h. After completion of the reaction, the crude material concentrated under reduced pressure. The desired product was directly purified by flash column chromatography in silica gel with pentane/EtOAc.

Reference： [1]Patent: WO2019/96832,2019,A1 .Location in patent: Page/Page column 33; 38; 39
[2]Journal of the American Chemical Society,2018,vol. 140,p. 12200 - 12209
[3]Advanced Synthesis and Catalysis,2020,vol. 362,p. 2367 - 2372

62
[ 459-31-4 ]
[ 13633-25-5 ]
C₁₉H₂₁FO [ No CAS ]