197223-39-5|(3,5-Di-tert-butylphenyl)boronic acid| Ambeed

CAS No. :	197223-39-5
Formula :	C₁₄H₂₃BO₂
M.W :	234.14
SMILES Code :	CC(C1=CC(C(C)(C)C)=CC(B(O)O)=C1)(C)C
MDL No. :	MFCD07780212
InChI Key :	RPCBIEHUQSGPNA-UHFFFAOYSA-N
Pubchem ID :	11470330

Safety of [ 197223-39-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 197223-39-5 ]

* 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 [ 197223-39-5 ]

[ 197223-39-5 ] Synthesis Path-Downstream 1~54

1
[ 916235-51-3 ]
[ 197223-39-5 ]
[ 916235-54-6 ]

References: [1]Tetrahedron,2006,vol. 62,p. 11425 - 11436.

2
(R)-3,3'-bis(4-trifluoromethanesulfonyloxyphenyl)-2,2'-dimethyl-1,1'-binaphthyl [ No CAS ]
[ 197223-39-5 ]
(R)-3,3'-bis(4-(3,5-di-tert-butylphenyl)phenyl)-2,2'-dimethyl-1,1'-binaphthyl [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 16044 - 16045.

3
[ 22385-77-9 ]
[ 197223-39-5 ]

Yield	Reaction Conditions	Operation in experiment
		Bromo-3,5-di-tert-butylbenzene (1.3 g, 5 mmole) was dissolved in THF (20 mL), to this solution was slowly added n-BuLi (1.6 M, 3.3 mL) at -78° C., the reaction was stirred at this temperature for 30 min, trimethyl borate (0.75 g, 7.5 mmole) was added all at once, stir over night while the reaction was allowed to slowly warm up to room temperature. Hydrochloric acid (6N, 5 mL) was added and stirred for 3 hrs at room temperature. Water (200 mL) was added, and the precipitate was collected, washed with water (10 mL.x.3), dried under vacuum to give titled compound.

References: [1]Journal of Chemical Sciences,2011,vol. 123,p. 555 - 565.
[2]Canadian Journal of Chemistry,2006,vol. 84,p. 1487 - 1503.
[3]Patent: US2009/30012,2009,A1 .Location in patent: Page/Page column 23.
[4]Chemical Communications,2011,vol. 47,p. 7341 - 7343.

4
[ 22385-77-9 ]
C₂₈H₄₆B₂O₄ [ No CAS ]
C₄₂H₆₉B₃O₆ [ No CAS ]
[ 197223-39-5 ]

References: [1]Chemistry - A European Journal,2007,vol. 13,p. 4433 - 4451.

5
[ 1460-02-2 ]
[ 197223-39-5 ]

References: [1]Chemistry - A European Journal,2007,vol. 13,p. 4433 - 4451.
[2]Chemical Communications,2015,vol. 51,p. 1926 - 1929.

6
[ 2380-36-1 ]
[ 197223-39-5 ]

References: [1]Canadian Journal of Chemistry,2006,vol. 84,p. 1487 - 1503.

Yield	Reaction Conditions	Operation in experiment
		3,5-di-tert-butylphenylboronic acid (Compound 9) To a cold (-78° C.) solution of 3,5-tert-butyl bromobenzene (available from Lancaster Co., 2.1 g, 8.2 mmol) in tetrahydrofuran (THF) (20 mL) was added t-BuLi (1.7M solution in pentane, 9.7 mL, 16.4 mmol) dropwise. The mixture was stirred for 1 hour between -78° C. and -20° C. The reaction was cooled to -78° C. and trimethylborate (1.7 g, 16.4 mmol) was added via syringe dropwise. The mixture was stirred and gradually warmed to ambient temp. over 1 hour and quenched with aqueous ammonium chloride solution. The mixture was extracted with ethylacetate (3*30 mL), the combined organic layer was washed with brine, dried and the solvent was removed. The crude product was used in the next step without further purification.

8
[ 197223-39-5 ]
(S)-(2,2'-dimethyl-1,1’binaphthalene)-3,3’-diylbis(trifluoromethanesulfonate) [ No CAS ]
C₅₀H₅₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With barium dihydroxide;palladium diacetate; triphenylphosphine; In Dimethyl ether; water; for 7h;Heating / reflux;	The compound 22 (S-form) and <strong>[197223-39-5]3,5-di-tert-butylphenyl boronic acid</strong> in 2 equivalents to the compound 22 were subjected to a Suzuki coupling reaction in barium hydroxide hexahydrate in 3 equivalents to the compound 22, 5 mol percent of palladium acetate and 1.2 mol percent of triphenylphosphine in water and dimethyl ether for 7 hours under reflux. The resulting mixture was cooled to room temperature, and a saturated ammonium chloride solution was added thereto, and the mixture was extracted with ethyl ether to give a compound 28 in a 88percent yield. Then, the compound 28 was refluxed together with 2 equivalents of NBS and 0.1 equivalents of AIBN in benzene for one hour and concentrated, and then subjected to silica gel column chromatography to give a compound 29 in a 77percent yield.

References: [1]Patent: EP1712549,2006,A1 .Location in patent: Page/Page column 67.
[2]Chemical Record,2013,vol. 13,p. 117 - 127.

9
[ 197223-39-5 ]
(S)-diisopropyl 3,3'-dibromo-1,1'-binaphthyl-2,2'-dicarboxylate [ No CAS ]
C₅₆H₆₆O₄ [ No CAS ]

References: [1]Tetrahedron Letters,2008,vol. 49,p. 2026 - 2030.

10
[ 121-43-7 ]
[ 22385-77-9 ]
[ 197223-39-5 ]

Yield	Reaction Conditions	Operation in experiment
91%		1-Bromo-3,5-di-t-butylbenzene and 40 mL of tetrahydrofuran were put in a 100-mL glass reactor, and cooled to ?70° C. in a dry ice-heptane bath. 16.4 mL (40.9 mmol) of n-butyllithium-n-hexane solution (2.5 mol/L) was dropwise added thereto, and stirred for 30 minutes. Subsequently at ?78° C., 4.25 g (40.9 mmol) of trimethyl borate was added and stirred for 2 hours, and further stirred at room temperature for 12 hours. An aqueous 1 M hydrogen chloride solution was added to the reaction liquid until the pH of the liquid could reach 3, then transferred into a separatory funnel, extracted three times with t-butyl methyl ether, and dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated under reduced pressure, and the resultant crude product was purified through silica gel column chromatography (developing solvent, petroleum ether/ethyl acetate=20/1) to give 8.00 g (yield 91percent) of 3,5-di-t-butylphenylboronic acid as a pale yellow solid
	With hydrogenchloride; In tetrahydrofuran; diethyl ether; water;	Synthesis of (3,5-di-tert-butylphenyl)boronic acid.10.0 g of 1-Bromo-3,5-di-tert-butylbenzene (37.1 mmol) in 20 ml THF was added dropwise to a suspension of 1.26 g Mg turnings (51.9 mmol) in 30 ml THF.After complete addition the mixture was stirred at reflux for 2.5 h.Subsequently the warm Grignard solution was transferred via canula into a dropping funnel and added dropwise to a solution of 5.77 g trimethyl borate (55.6 mmol) in 100 mL Et2O.During the addition the temperature was kept below - 60 °C.After complete addition the mixture was warmed to room temperature and stirred over night.The reaction was quenched by adding 55.8 ml H2O and 5.6 mL conc. HCl.The organic phase was separated and the aqueous phase was extracted several times with Et2O.The combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate.Evaporation of the solvent gave a white solid.Yield 7.59 g (88 percent).The boronic acid was obtained as a mixture of monomers and oligomers and used without further purification.

References: [1]Patent: JP5710035,2015,B2 .Location in patent: Paragraph 0169.
[2]Chemistry - A European Journal,2019,vol. 25,p. 3267 - 3271.
[3]Chemical Communications,2015,vol. 51,p. 1926 - 1929.
[4]Chemistry - A European Journal,2012,vol. 18,p. 4174 - 4178.
[5]Patent: EP2532687,2012,A2 .

11
[ 108-37-2 ]
[ 197223-39-5 ]
[ 1057337-53-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 100℃; for 5h;	A mixture of 3,5-di-tert-butylbenzeneboronic acid (175 mg, 0.75 mmole), Bromo-3-chlorobenzene (94 mg, 0.5 mmole), PdCl2(PPh3)2 (10 mg), DME (1.5 mL) and Na2CO3 solution (2N, 0.5 mL) was degassed and stirred at 100° C. for 5 hrs, and allowed to cool down to room temperature, diluted with 5 mL ethyl acetate, dried over sodium sulfate, filtered and concentrated. Column chromatography yield pale yellowish oil as product

References: [1]Patent: US2009/30012,2009,A1 .Location in patent: Page/Page column 24.

12
[ 1057337-55-9 ]
[ 197223-39-5 ]
[ 1057337-57-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 100℃; for 5h;	A mixture of 3,5-di-tert-butylbenzeneboronic acid (175 mg, 0.75 mmole), the chloro-pyrazine prepared in Example 12 Step 1 (142 mg, 0.5 mmole), PdCl2(PPh3)2(10 mg), DME (1.5 mL) and Na2CO3 solution (2N, 0.5 mL) was degassed and stirred at 100° C. for 5 hrs, and allowed to cool down to room temperature, diluted with 5 mL ethyl acetate, dried over sodium sulfate, filtered and concentrated. Column chromatography yield pale yellowish oil as product.

References: [1]Patent: US2009/30012,2009,A1 .Location in patent: Page/Page column 23.

13
[ 1098071-09-0 ]
[ 197223-39-5 ]
[ 1098071-11-4 ]

References: [1]Organometallics,2009,vol. 28,p. 465 - 472.

14
(R)-3,3'-dibromo-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-diamine [ No CAS ]
[ 197223-39-5 ]
(R)-3,3'-bis(3,5-di-4-tert-butylphenyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine [ No CAS ]

References: [1]Chemical Communications,2009,p. 1956 - 1958.

15
[ 59489-71-3 ]
[ 197223-39-5 ]
[ 1220531-17-8 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 1401 - 1403.

16
[ 1202963-84-5 ]
[ 197223-39-5 ]
[ 1202963-85-6 ]

References: [1]Chemical Communications,2009,p. 6961 - 6963.

17
[ 5176-27-2 ]
[ 197223-39-5 ]
[ 1261292-09-4 ]

References: [1]Organic Letters,2011,vol. 13,p. 632 - 635.

18
[ 197223-39-5 ]
[ 1261292-10-7 ]

References: [1]Organic Letters,2011,vol. 13,p. 632 - 635.

19
[ 197223-39-5 ]
C₅₇H₆₀N₂ [ No CAS ]

References: [1]Organic Letters,2011,vol. 13,p. 632 - 635.

20
[ 197223-39-5 ]
[ 1261467-84-8 ]

References: [1]Organic Letters,2011,vol. 13,p. 632 - 635.

21
[ 3460-24-0 ]
[ 197223-39-5 ]
[ 1244947-50-9 ]

References: [1]Journal of Physical Chemistry B,2010,vol. 114,p. 12765 - 12776.

22
[ 197223-39-5 ]
[ 1244947-51-0 ]

References: [1]Journal of Physical Chemistry B,2010,vol. 114,p. 12765 - 12776.

23
[ 626-39-1 ]
[ 197223-39-5 ]
[ 120046-02-8 ]