171408-84-7|2,7-Dibromo-9,9'-spirobifluorene| Ambeed

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Quality Control of [ 171408-84-7 ] Purity: 98% SDS Specification

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Product Citations

Versatile Nanoporous Organic Polymer Catalyst for the Size- Selective Suzuki-Miyaura Coupling Reaction

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon ; Swager, Timothy M. ;

DOI: 10.1021/acsanm.2c04393 ACS Appl. Nano Mater.,2022,5(12):18603-18611.

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki−Miyaura coupling reaction ; size-selective reaction ; catalyst processing

Purchased from AmBeed: 128796-39-4 ; 10365-98-7 ; 98-80-6 ; 556-96-7 ; 171663-13-1 ; 71597-85-8 ; 402-43-7 ; 2042-37-7 ; 22385-77-9 ; 16419-60-6 ; 15862-18-7 ; 87199-15-3 ; 171408-84-7 ; 643-58-3 ; 591-50-4 ; 76911-73-4 ; 398-36-7 ; 14871-92-2 ; 5720-07-0 ; 945976-76-1 ; 366-18-7 ; 2920-38-9 ; 623-00-7 ; 24973-49-7 ; 588-59-0 ; 128796-39-4 ; 5723-93-3 ; 17057-88-4 ; 126485-55-0

Product Details of [ 171408-84-7 ]

CAS No. :	171408-84-7
Formula :	C₂₅H₁₄Br₂
M.W :	474.19
SMILES Code :	BrC1=CC2=C(C=C1)C3=C(C=C(Br)C=C3)C24C5=C(C6=C4C=CC=C6)C=CC=C5
MDL No. :	MFCD08704218
InChI Key :	UPJLZKCEPFAKSH-UHFFFAOYSA-N
Pubchem ID :	15544767

Safety of [ 171408-84-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 171408-84-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	27
Num. arom. heavy atoms	24
Fraction Csp3	0.04
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	118.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	4.22
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	7.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	7.56
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	7.23
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	7.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	6.93

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-8.33
Solubility	0.00000224 mg/ml ; 0.0000000047 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-7.6
Solubility	0.0000118 mg/ml ; 0.0000000249 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-11.76
Solubility	0.0000000008 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-3.68 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.75

Application In Synthesis of [ 171408-84-7 ]

* 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 [ 171408-84-7 ]

[ 171408-84-7 ] Synthesis Path-Downstream 1~35

1
[ 188290-36-0 ]
[ 171408-84-7 ]
2,7-bis(2-thienyl)-9,9'-spirobifluorene [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.

2
[ 1081-34-1 ]
[ 171408-84-7 ]
2,7-bis(2,2':5',2''-terthiophen-5-yl)-9,9'-spirobifluorene [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.

3
[ 492-97-7 ]
[ 171408-84-7 ]
2,7-bis(2,2'-bithiophen-5-yl)-9,9'-spirobifluorene [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.

4
[ 544-92-3 ]
[ 171408-84-7 ]
[ 497955-48-3 ]

References: [1]Chemical Communications,2002,p. 2874 - 2875.
[2]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.

5
[ 122-39-4 ]
[ 171408-84-7 ]
N,N,N',N'-tetrakisphenyl-9,9'-spirobifluorene-2,7-diamine [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.
[2]Chemical Communications,2002,p. 2874 - 2875.

6
4-hexyl-2-thienylzinc chloride [ No CAS ]
[ 171408-84-7 ]
[ 445498-67-9 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.

7
[ 171408-84-7 ]
C₂₀H₂₉ClS₂Zn [ No CAS ]
[ 445498-69-1 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.

8
[ 171408-84-7 ]
sodium 4-hexyl-2-thienyl trihydroxyboranuide [ No CAS ]
[ 445498-67-9 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.

9
[ 171408-84-7 ]
C₃₀H₄₃ClS₃Zn [ No CAS ]
C₈₅H₁₀₀S₆ [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.

10
[ 171408-85-8 ]
[ 171408-84-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	hydrogenchloride; In water; acetic acid; for 12h;Heating / reflux;	2) Synthesis of a compound 2 After the compound 1 (14.28 mmol, 7 g) was dissolved in 70 ml of acetic acid, three drops of concentrated HCl were added thereto, and refluxing was conducted for 12 hours. After the reaction, the resulting mixture was slowly dropped into 250 ml of water to produce a precipitate. After the precipitate was dried, purification was conducted using a developer having hexane and ethyl acetate in a volume ratio of 10:1 to produce a compound 2 (12.72 mmol, 6 g) (Yield 89 percent).
86%	With acetic acid; at 120℃; for 24h;	Under the protection of argon, add 2,7-dibromofluorenone 10 mmol to the reaction flask.11mmol of 2-fluorobiphenyl and 20ml of tetrahydrofuran solvent, after stirring evenly,22 mmol of lithium metal tablets were added to the reaction solution in batches.Then, the temperature is raised to about 40 ° C, and the reaction is carried out for 24 hours.After the reaction was completed and returned to room temperature, the reaction was quenched with 20 mL of 1N aqueous hydrochloric acid.The organic phase was separated, and the tetrahydrofuran was evaporated to dryness on a rotary evaporator.The crude solid was added to 10 ml of acetic acid.Heating to 120 ° C for 24 hours, after the end of the ring closure reactionFiltration gave crude 2,7-dibromo-9,9'-spirobifluorene.The crude product uses a mixed solvent of dichloromethane and n-hexane as an eluent.Perform column chromatography separation, and the chromatographic silica gel is 200-300 mesh.Finally, the product 2,7-dibromo-9,9'-spirobifluorene 4.08g was obtained.The yield was 86percent.
82%	With hydrogenchloride; acetic acid; In water; for 1h;Reflux;	2-iodobiphenyl 1mol was dissolved in THF after the dropwise addition of n-BuLi at -78 a stirred for 1 hour After dropwise dissolving 2,7-dibromo-9H-fluoren-9-one 1mol in THF. The temperature was raised to room temperature and then stirred for one hour to confirm the completion of the reaction and extracted with CH2Cl2 and 1N HCl. The organic layer was dried over MgSO4 to give the Intermediate K was purified by column chromatography and recrystallized (yield 71percent). After the K intermediate was dissolved in acetic acid to complete the addition of concentrated hydrochloric acid for 1 hour under reflux reaction. It was extracted using ether and water and the organic layer was washed with mwot Sat NaHCO3. The organic layer was dried over MgSO4 and purified by column chromatography and recrystallization to give the intermediate L (Yield 82percent).

80%	With sulfuric acid; In toluene; at 20℃; for 2h;	To 180 g of a toluene solution of 9- (2-biphenyl) -2,7-dibromo-9-fluorene alcohol obtained in Example 3,Concentrated sulfuric acid 18.0 g (0.180 mol, 2.00 M.R.) was charged,The reaction was carried out at room temperature for 2 hours.After caustic water was added to the obtained reaction mixture solution to neutralize it,Toluene was added to crystallize,By filtration and drying,35.9 g of 2,7-dibromo-9,9'-spirobifluorene as white crystals(Yield: 80percent, total yield from Example 3: 72percent, purity: 95percent).
57%	With hydrogenchloride; In acetic acid; at 50℃;Heating / reflux;	22 g (45.0 mmol) of 9-biphenyl-2-yl-2,7-dibromo-9-fluorenol, and 100 mL of glacial acetic acid were placed in a 300 mL three-necked flask, several drops of concentrated hydrochloric acid were added, and the mixture was refluxed. After the reaction, the precipitates were filtered The precipitate was recrystallized with ethanol, and 12.3 g of 2,7-dibromo-spiro-9,9'-bifluorene was obtained as a white solid, in a yield of 57percent. [0359]A synthesis scheme (h-4) of 2,7-dibromo-9,9'-spiro-bifluorene is shown below. [0360]
	With hydrogenchloride; for 4h;Reflux;Product distribution / selectivity;	Diethyl ether (10 mL) was added to magnesium (1.9 g, 25.6 mmol), and 2-bromobiphenyl (5 g, 21.6 mmol) diluted in diethyl ether (20 mL) was slowly added dropwise, and the mixture was stirred under reflux for 3 hours. In diethyl ether (40 mL), dissolved was 2,7-dibromofluorenone (6.7 g, 20 mmol), and the solution was added to the mixture previously prepared. The resultant mixture was stirred under reflux for 12 hours, and cooled to ambient temperature. The precipitate produced was filtered under reduced pressure, and dissolved in acetic acid (40 mL). While heating the solution under reflux, concentrated hydrochloric acid was slowly added dropwise thereto. After four hours, the reaction was completed to give Compound (126) (5.2 g, 10.9 mmol).

References: [1]Patent: EP1777227,2007,A1 .Location in patent: Page/Page column 6-7.
[2]Macromolecules,2010,vol. 43,p. 10355 - 10365.
[3]Patent: CN108863694,2018,A .Location in patent: Paragraph 0039; 0040.
[4]Patent: KR101555155,2015,B1 .Location in patent: Paragraph 0119; 0120; 0121; 0122.
[5]Patent: JP6257340,2018,B2 .Location in patent: Paragraph 0050.
[6]Patent: WO2007/43354,2007,A1 .Location in patent: Page/Page column 101.
[7]Journal of the American Chemical Society,2002,vol. 124,p. 11576 - 11577.
[8]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.
[9]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 32.
[10]Advanced Functional Materials,2010,vol. 20,p. 4152 - 4161.
[11]Journal of the American Chemical Society,2017,vol. 139,p. 11073 - 11080.
[12]Chemical Communications,2018,vol. 54,p. 642 - 645.

11
[ 61676-62-8 ]
[ 171408-84-7 ]
[ 728911-52-2 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11576 - 11577.

12
[ 171408-84-7 ]
[ 317802-08-7 ]
polymer; monomer(s): 2,7-bis(1,3,2-dioxaboran-2-yl)-9,9-dioctylfluorene; spiro[fluorene-9,9-2,7-dibromofluorene] [ No CAS ]

References: [1]Analytical Chemistry,2002,vol. 74,p. 6252 - 6258.

13
[ 50-00-0 ]
[ 171408-84-7 ]
[ 773877-89-7 ]

References: [1]Macromolecules,2004,vol. 37,p. 7197 - 7202.

14
[ 825655-29-6 ]
[ 171408-84-7 ]
C₁₅₁H₁₉₂ [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 4845 - 4848.

15
[ 934708-07-3 ]
[ 171408-84-7 ]
C₇₇H₇₂O₂ [ No CAS ]

References: [1]Synlett,2007,p. 231 - 234.

16
[ 171408-84-7 ]
[ 171408-88-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With iodine; bis-[(trifluoroacetoxy)iodo]benzene; In chloroform; at 20℃; for 12h;	92.0 g (194.1 mmol) of 2,7-dibromospirobifluorene were dissolved in 200 ml of CHCl3, after which 100.1 g (233 mmol) of bis(trifluoroacetoxy)iodobenzene and 59.0 g of I2 were added and the mixture was stirred at RT under nitrogen for 12 hours. The suspension was filtered, the residue washed with CHCl3 and recrystallized twice from 1,4-dioxane. The yield of the diiodated spirobifluorene was 121.4 g (86percent) at a purity of >99percent (1H-NMR). 1H NMR (DMSO-d6, 500 MHz)-8.04 (d, 3JHH=7.9 Hz, 2H), 7.88 (d, 3JHH=7.9 Hz, 2H), 7.82 (dd, 3JHH=7.9 Hz, 4JHH=1.5 Hz, 2H), 7.66 (dd, 3JHH=8.3 Hz, 4JHH=1.9 Hz, 2H), 6.98 (d, 4JHH=1.2 Hz, 2H), 6.83 (d, 4JHH=1.5 Hz, 2H).

References: [1]Patent: US2007/265473,2007,A1 .Location in patent: Page/Page column 17.

17
[ 123324-71-0 ]
[ 171408-84-7 ]
2,7-bis(4-tert-butylphenyl)-9,9'-spirobifluorene [ No CAS ]

References: [1]Chemical Communications,2007,p. 1831 - 1833.

18
[ 171408-84-7 ]
[ 876173-76-1 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.

19
[ 171408-84-7 ]
[ 876173-77-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.

20
[ 171408-84-7 ]
[ 873657-58-0 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.
[2]Chemical Communications,2002,p. 2874 - 2875.

21
[ 171408-84-7 ]
[ 876173-86-3 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.
[2]Chemical Communications,2002,p. 2874 - 2875.

22
[ 171408-84-7 ]
[ 497955-49-4 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.
[2]Chemical Communications,2002,p. 2874 - 2875.

23
[ 171408-84-7 ]
C₄₉H₄₀N₄O₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 456 - 465.
[2]Chemical Communications,2002,p. 2874 - 2875.

24
[ 171408-84-7 ]
[ 773877-91-1 ]

References: [1]Macromolecules,2004,vol. 37,p. 7197 - 7202.

25
[ 171408-84-7 ]
[ 773877-93-3 ]

References: [1]Macromolecules,2004,vol. 37,p. 7197 - 7202.

26
[ 14348-75-5 ]
[ 171408-84-7 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11576 - 11577.
[2]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.
[3]Patent: US2011/54229,2011,A1 .
[4]Macromolecules,2010,vol. 43,p. 10355 - 10365.
[5]Advanced Functional Materials,2010,vol. 20,p. 4152 - 4161.
[6]Patent: KR101555155,2015,B1 .
[7]Journal of the American Chemical Society,2017,vol. 139,p. 11073 - 11080.

27
[ 82214-69-5 ]
[ 171408-84-7 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11576 - 11577.

28
[ 2052-07-5 ]
[ 171408-84-7 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 4924 - 4936.
[2]Patent: US2011/54229,2011,A1 .
[3]Advanced Functional Materials,2010,vol. 20,p. 4152 - 4161.

29
[ 536-74-3 ]
[ 171408-84-7 ]
2,7-bis(phenylethynyl)-9,9'-spyrobifluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.7%	With piperidine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 20 - 110℃; for 12h;	10 g (21.09 mmol) of 2.7-dibromo-9.9'-spyrobifluorene, 0.43 g (0.63 mmol) of bistriphenylphosphine palladium dichloride and 0.12 g (0.63 mmol) of copper iodide were put into a 500 ml three-neck round bottom flask equipped with a stirrer, a thermometer and a reflux condenser under an argon atmosphere, and then 300 ml of piperidine was added thereto so as to dissolve the resultant. 5.38 g (52.61 mmol) of phenylacetylene was gradually dropped thereto at room temperature. After completion of the dropping, the temperature of the reaction mixture was gradually raised to 110° C. and then stirred at 110° C. for 12 hours. When the reaction was completed, the reaction mixture was cooled down to room temperature. Generated salt was filtered off, and then the filtrate was concentrated under a reduced pressure. The residue was dissolved in dichloromethane, washed with water several times and then dried with anhydrous magnesium sulfate, which was then filtered off. The solvent was removed, and the residue was re-crystallized from a mixture of ethyl acetate and hexane to obtain yellow crystal, which was dried sufficiently in a vacuum oven at 40° C. to give 6.52 g (59.7percent yield) of [M-10], of which melting point was 210-212° C. 1H NMR (CDCl3), delta=6.74-6.78(d, 2H, aromatic), 6.90(s, 2H, aromatic), 7.10-7.18(t, 2H, aromatic), 7.24-7.28(m, 6H, aromatic), 7.36-7.42(m, 6H, aromatic), 7.52-7.57(d, 2H, aromatic) 7.79-7.88(t, 4H, aromatic).

References: [1]Patent: US2005/67955,2005,A1 .Location in patent: Page/Page column 9.

30
[ 419536-33-7 ]
[ 171408-84-7 ]
H-5 [ No CAS ]

References: [1]Patent: WO2005/123634,2005,A1 .Location in patent: Page/Page column 55.

31
[ 2052-07-5 ]
[ 6344-61-2 ]
[ 14348-75-5 ]
[ 171408-84-7 ]

Yield	Reaction Conditions	Operation in experiment
11 g (77%)	With ammonium chloride; magnesium; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether; acetic acid;	c 2,7-Dibromo-9,9'-spirobifluorene A Grignard reagent prepared from 0.72 g (30 mmol) of magnesium turnings and 5.1 ml (30 mmol) of 2-bromobiphenyl in 15 ml of diethyl ether was added dropwise while stirring (in an ultrasonic bath) to a boiling suspension of 10.0 g (29.6 mmol) of 2,7-dibromo-9-fluorenone in 100 ml of dry diethyl ether over a period of 2 hours. After addition was complete, the mixture was boiled for a further 3 hours. After cooling overnight, the precipitate formed was filtered off with suction and washed with cold ether. The magnesium complex which had been filtered off with suction was hydrolyzed in a solution of 15 g of ammonium chloride in 250 ml of ice water. After 1 hour, the 9-(2-biphenylyl)-2,7-dibromo-9-fluorenol formed was filtered off with suction, washed with water and sucked dry. For the ring closure reaction, the dried fluorenol was boiled in 100 ml of glacial acetic acid, after addition of 3 drops of 30 concentrated HCl, for 6 hours. The mixture was allowed to crystallize overnight, the product formed was filtered off with suction and washed with glacial acetic acid and water. Yield: 11 g (77percent) of 2,7-dibromo-9,9'-spirobifluorene. This was purified further by recrystallization from THF. 1H-NMR (CDCl3, ppm): 6.73 (d, J=7.63 Hz, 2 H, H-1',8'); 6.84 (d, J=1.83 Hz, 2 H, H-1,8); 7.15 (td, J=7.63, 1.22 Hz, 2 H, H-2',7'); 7.41 (td, J=7.63, 1.22 Hz, 2 H, H-3',6'); 7.48 (dd, J=8.24, 1.83 Hz, 2 H, H-3,6); 7.67 (d, J=8.24; 2 H; H-4,5); 7.85 (d, J=7.63, 2 H, H-4',5').
11 g (77%)	With hydrogenchloride; ammonium chloride; magnesium; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether; acetic acid;	Example 1 Synthesis of 2,7-dibromo-9,9'-spirobifluorene A Grignard reagent prepared from 0.72 g (30 mmol) of magnesium turnings and 5.1 ml (30 mmol) of 2-bromobiphenyl in 15 ml of diethyl ether is added dropwise over the course of 2 hours while stirring (in an ultrasonic bath) to a boiling suspension of 10.0 g (29.6 mmol) of 2,7-dibromo-9-fluorenone in 1 00 ml of dry diethyl ether. After addition is complete, the mixture is boiled for a further 3 hours. After cooling overnight, the precipitate formed is filtered off with suction and washed with cold ether. The magnesium complex filtered off is hydrolyzed in a solution of 15 g of ammonium chloride in 250 ml of ice water. After 1 hour, the 9-(2-biphenylyl)-2,7-dibromo-9-fluorenol formed is filtered off with suction, washed with water and sucked dry. For the ring closure reaction, the dried fluorenol is boiled in 100 ml of glacial acetic acid, after addition of 3 drops of concentrated hydrochloric acid, for 6 hours. The mixture is allowed to crystallize overnight, the product formed is filtered off with suction and washed with glacial acetic acid and water. Yield: 11 g (77percent) of 2,7-dibromo-9,9'-spirobifluorene. It can be further purified by recrystallization from THF. 1 H-NMR (CDCl3, ppm): 6.73 (d, J=7.63 Hz, 2H, H-1',8'); 6.84 (d, J=1.83 Hz, 2H, H-1,8); 7.15 (td, J=7.63, 1.22 Hz, 2H, H-2',7'); 7.41 (td, J=7.63, 1.22 Hz, 2H, H-3',6'); 7.48 (dd, J=8.24, 1.83 Hz, 2H, H-3,6); 7.67 (d, J=8.24; 2H; H-4,5); 7.85 (d, J=7.63, 2H, H-4',5').
11 g (77%)	With ammonium chloride; magnesium; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether; acetic acid;	l) Synthesis of 2,7-dibromo-9,9'-spirobifluorene The Grignard reagent prepared from 0.72 g (30 mmol of magnesium turnings and 5.1 ml (30 mmol) of 2-bromobiphenyl in 15 ml of diethyl ether is added dropwise over a period of 2 hours, while stirring (in an ultrasonic bath), to a boiling suspension of 10.0 g (29.6 mmol) of 2,7 dibromo-9-fluorenone in 100 ml of dry diethyl ether. After the addition is complete, the mixture is boiled for a further 3 hours. After cooling overnight, the precipitated solid is filtered off with suction and washed with cold ether. The magnesium complex filtered off is hydrolyzed in a solution of 15 g of ammonium chloride in 250 ml of ice water. After 1 hour, the 9-(2-biphenylyl)-2,7-dibromo-9-fluorenol formed is filtered off with suction, washed with water and sucked dry. For the ring-closure reaction, the dried fluorenol is boiled in 100 ml of glacial acetic acid for 6 hours, after addition of 3 drops of concentrated HCI. The mixture is allowed to crystallize overnight, the product formed is filtered off with suction and is washed with glacial acetic acid and water. Yield: 11 g (77 percent) of 2,7-dibromo-9,9'-spirobifluorene. It can be further purified by recrystallization from THF. 1H-NMR (CDCl3, ppm): 6.73 (sd, J = 7.63 Hz, 2 H, H-1',8'); 6.84 (d, J = 1.83 Hz, 2 H, H-1,8); 7.15 (td, J = 7.63, 1.22 Hz, 2 H, h-2',7'); 7.41 (td, J = 7.63, 1.22 Hz, 2H, H-3',6'); 7.48 (dd, J = 8.24, 1.83 Hz, 2H, H-3,6); 7.67 (d, J = 8.24 Hz; 2 H; H-4,5); 7.85 (d, J= 7.63, 2H, H-4',5').

References: [1]Patent: US2003/111107,2003,A1 .
[2]Patent: US5621131,1997,A .
[3]Patent: EP1053578,2002,B1 .

32
[ 171408-84-7 ]
[ 128055-74-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bromine; In chloroform; at 0℃; for 3h;	3) Synthesis of a compound 3 The compound 2 (10.6 mmol, 5 g) was dissolved in 150 ml of chloroform and cooled to 0°C, bromine (21.19 mmol, 3.39 g) was slowly dropped thereon, and agitation was conducted for 3 hours. After the reaction, 50 ml of 2 M potassium hydroxide was injected into the reaction vessel to bring about neutralization. The reactants were then washed three times using distilled water. Next, an organic layer was separated and subjected to vacuum distillation, and the resulting solid was recrystallized using a mixed solution of chloroform and ethanol to produce a compound 3 (9.01 mmol, 5.65 g) (Yield 85 percent).

References: [1]Patent: EP1777227,2007,A1 .Location in patent: Page/Page column 6-7.

33
[ 19606-98-5 ]
[ 171408-84-7 ]
DPA₂SF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 6h;	5.0 g (10.6 mmol) of 2, 7-dibromo-spiro-9,9'-bifluorene, 7.4 g (21.0 mmol) of DPA, 63 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0), and 3.6g (37 mmol) of t-butoxysodium were placed in a 300 mL three-necked flask, and nitrogen substitution was conducted. 100 mL of toluene was added to the mixture, and the mixture was degassed at reduced pressure. 0.05 mL of tri(t-butyl)phosphine (10 wtpercent hexane solution) was added, and the mixture was stirred for 6 hours at 8O0C. After the reaction, the mixture was filtered through Celite. The filtrate was washed 3 times with EPO <DP n="103"/>water and once with a saturated saline solution, then dried with magnesium sulfate. The reaction mixture was naturally filtered, and the filtrate was concentrated to obtain an oily product. This oily product was purified by silica gel column chromatography (hexane:ethyl acetate = 7:3), and recrystallized with chloroform and ethanol, giving 6.0 g of a pale yellow powdered solid in a yield of 57percent. It was confirmed that this pale yellow powdered solid was DPA2SF by a nuclear magnetic resonance method (NMR). [0363]1H NMR of the compound obtained is shown below. Also, a 1H NMR chart is shown in FIG. 27.1H NMR (300 MHz, DMSO-d6), delta=7.84 (d, J= 7.21 Hz, 2H), 7.77 (d, J= 7.80 Hz, 2H), 7.32-7 79 (m, 40H), 6.73 (d, J= 7.80 Hz, 2H), 6.16 (d, J= 2.10 Hz, 2H) [0364]A synthesis scheme (i-1) of DPA2SF is shown below. [0366]Sublimation purification was conducted on 2.0 g of the DPA2SF for 24 hours at a pressure of 6.7 Pa and a temperature of 3500C. 1.3 g was recovered, in a yield of 66percent.

References: [1]Patent: WO2007/43354,2007,A1 .Location in patent: Page/Page column 101-102.

34
[ 2052-07-5 ]
[ 14348-75-5 ]
[ 171408-84-7 ]

References: [1]Synthetic Communications,2008,vol. 38,p. 1888 - 1895.
[2]Chemistry - An Asian Journal,2016,vol. 11,p. 2555 - 2563.
[3]Angewandte Chemie - International Edition,2018,vol. 57,p. 6696 - 6700.
Angew. Chem.,2018,vol. 130,p. 6806 - 6810,5.
[4]Chemical Communications,2018,vol. 54,p. 642 - 645.

35
[ 61676-62-8 ]
[ 171408-84-7 ]
(BO₂C(CH₃)2C(CH₃)2)OC₆H₃C(2,2'-biphenyl)C₆H₃O(C(CH₃)2C(CH₃)2BO₂) [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11576 - 11577.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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CAS No.: 171408-84-7

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