59785-43-2|3,5-Dibromoethylbenzene| Ambeed

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Quality Control of [ 59785-43-2 ] Purity: 95% SDS Specification

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Product Details of [ 59785-43-2 ]

CAS No. :	59785-43-2
Formula :	C₈H₈Br₂
M.W :	263.96
SMILES Code :	BrC1=CC(Br)=CC(CC)=C1
MDL No. :	MFCD11846036
InChI Key :	IHFAYHLKBUGUOQ-UHFFFAOYSA-N
Pubchem ID :	18711807

Safety of [ 59785-43-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 59785-43-2 ]

* 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 [ 59785-43-2 ]

[ 59785-43-2 ] Synthesis Path-Downstream 1~20

1
[ 4253-89-8 ]
[ 59785-43-2 ]
[ 849934-79-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tert.-butyl lithium; In tetrahydrofuran; pentane;	Preparation 1 Compounds of Formula (B) 1,3-Dibromo-5-ethyl-benzene (1.54 g, 5.8 mmoles) was dissolved into anhydrous THF (20 mL) under nitrogen, and was chilled to -78 C. To this stirring solution was slowly (over 10 min) added t-BuLi (3.8 mL, 6.5 mmoles, 1.7M solution in pentane). After the addition was complete the mixture was allowed to stir at -78 C. for an additional 30 min. After this period isopropyl disulfide (1.4 mL, 8.8 mmoles) was added and the mixture was allowed to warm to ambient temperature. The reaction was then warmed to 75 C., and was stirred at this temperature for 16 hours. After this period the reaction mix was evaporated in vacuo and was purified using flash silica chromatography (0-1% EtOAc/Hexane) to yield 1-bromo-3-ethyl-5-isopropylsulfanyl-benzene (1.08 g, 72%) as a clear liquid. 1H-NMR (CDCl3): δ 7.34-7.32 (m, 1H), 7.19-7.17 (m, 1H), 7.13-7.11 (m, 1H), 3.39 (m, J=6.6 Hz, 1H), 2.59 (q, J=7.6 Hz, 2H), 1.30 (d, J=6.6 hz, 6H), 1.22 (t, J=7.6 Hz, 3H).

References: [1]Patent: US2005/80111,2005,A1 .

2
[ 120359-56-0 ]
[ 59785-43-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogen;palladium hydroxide on carbon; In tetrahydrofuran; at 20℃; for 5h;	Step B 1, 3-Dibromo-5-ethyl-benzene A mixture of 1, 3-dibromo-5-vinyl-benzene (4.55 g, 17.4 mmol) and 20% Pd (OH) 2/C (2.0 g) in THF (60 mL) is purged with N2 and then H2, and the mixture is stirred under a H2 balloon at rt for 5 hours. The mixture is filtered through hyflo, and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 15/1 hexanes/ethyl acetate to afford 3.38 g (74%) of the title compound. Rf = 0.63 (9/1 hexanes/EtOAc).'H NMR (400 MHz, CDCl3).

References: [1]Patent: WO2005/37763,2005,A1 .Location in patent: Page/Page column 108.

3
[ 59785-43-2 ]
copper(l) cyanide [ No CAS ]
[ 1369782-16-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In N,N-dimethyl-formamide; at 150℃; for 3h;	Intermediate 583-Bromo-5-ethylbenzonitrile; A mixture of <strong>[59785-43-2]1,3-dibromo-5-ethylbenzene</strong> (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150 C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1]+.

References: [1]Patent: US2012/165347,2012,A1 .Location in patent: Page/Page column 36.

4
[ 59785-43-2 ]
[ 175205-85-3 ]

References: [1]Organic Letters,2016,vol. 18,p. 784 - 787.

5
[ 59785-43-2 ]
[ 14401-73-1 ]
2-bromo-1-(3,5-dibromophenyl)ethan-1-one [ No CAS ]

References: [1]Organic Letters,2016,vol. 18,p. 784 - 787.

6
[ 59785-43-2 ]
[ 98-80-6 ]
3-bromo-5-ethyl-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; ethanol; water; at 100℃; for 16h;Inert atmosphere;	General procedure: 3-Bromo-5-ethyl-1 ,1 '-biphenyl was synthesised according to general procedures GP13 - from 1 ,3- dibromo-5-ethybenzene (1 .50 g, 5.68 mmol), phenylboronic acid (0.62 g, 5.08 mmol), Pd(PPfi3)4 (0.65 g, 10 mol%), Na2C03 (1 .20 g, 1 1 .3 mmol), 1 ,4-dioxane (15 mL), ethanol (7.0 mL) and water (5.6 ml); 100 C, 16 h. Chromatographic purification (hexane) afforded a yellow oil (0.63 g, 47%). H NMR (400 MHz, DMSO-c/6) δ: 7.68-7.64 (m, 3H), 7.51 -7.39 (m, 5H), 2.68-2.66 (m, 2H), 1 .22 (t, J = 7.6 Hz, 3H). General procedures GP13 [00693] A mixture of bromide GP13_1 , Pd(PPh3)4, ArB(OR')2, Na2C03, H20, EtOH and toluene was degassed with argon and then stirred at 100 C for 16 h. After cooling to rt, the mixture was diluted with Et20 and filtered through celite. The organic solution was washed with H20, dried over Na2S04, filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography to afford biaryl GP13_2.

References: [1]Patent: WO2017/141049,2017,A1 .Location in patent: Paragraph 00692; 00693; 00884.

7
[ 460347-59-5 ]
[ 59785-43-2 ]
C₄₈H₃₄ [ No CAS ]