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Chemical Structure| 452-63-1 Chemical Structure| 452-63-1

Structure of 452-63-1

Chemical Structure| 452-63-1

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Product Details of [ 452-63-1 ]

CAS No. :452-63-1
Formula : C7H6BrF
M.W : 189.02
SMILES Code : CC1=CC(F)=CC=C1Br
MDL No. :MFCD00017921
InChI Key :RJPNVPITBYXBNB-UHFFFAOYSA-N
Pubchem ID :96743

Safety of [ 452-63-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 452-63-1 ]

* 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 [ 452-63-1 ]

[ 452-63-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 115309-58-5 ]
  • [ 452-63-1 ]
  • [ 733805-18-0 ]
YieldReaction ConditionsOperation in experiment
80% 3.4 g Magnesium (137.5 mmol) was suspended under argon in 12.0 ml tetrahydrofitrane and treated under reflux with a solution of 17.6 ml (137,3 mmol) 2-bromo-5- fluorotoluene in 20 ml TETRAHYDROFURANE. After the addition of the first 3 ml of this solution, the mixture was warmed to start the Grignard reaction. The reaction mixture was stirred for 30 minutes under reflux, cooled to 50 C and added within 10 minutes to a solution of 10. 0 G (97 %, 45 mmol) N-TERT-BUTYL-6-CHLORONICOTINAMIDE in 50 ml TETRAHYDROFURANE (exothermic reaction). The mixture was stirred at 70 C for 2 hours, cooled to room temperature and a solution of 17.4 G (68, 6 mmol, 1.5 eq. ) iodine in 100 ml TETRAHYDROFURANE was added slowly (exothermic reaction). The resulting suspension was stirred for 1.7 hours at 50 C, treated at room temperature with 50 ml water, poured onto 150 ml 2 N aqueous sulfuric acid and treated with 150 ml tert-butyl-methyl-ether. After vigorous stirring, the phases were separated and the organic phase was washed with half-saturated aqueous sodium bicarbonate and with half-saturated aqueous sodium chloride. The aqueous phases were extracted with tert-butyl-methyl-ether. The combined organic extracts were dried, concentrated in a rotary evaporator and dried under high vacuum at room temperature to provide 17.3 g of a yellow oil. This oil was dissolved in dichloromethane and filtered through silica gel eluting with hexane and then with dichloromethane. The fractions with the product were collected and concentrated under reduced pressure to a volume of ca. 200 ml to which 400 ml hexane was added. The solution was concentrated in a rotary evaporator to a volume of ca. 150 ml, the suspension obtained was treated with 200 ml hexane and stirred for 2 hours at 4 C. The precipitate was filtered off, washed with cold hexane/ethyl acetate 19/1 (-20C) and dried under high vacuum to yield 8.0 g (55 %) N-FERT-BUTYL-6-CHLORO-4- (4-NUORO-2-METHYL- phenyl) -nicotinamide as a light beige powder. The mother liquors were concentrated in a rotary evaporator PROVIDING 8. 5 G of an orange solid, which was purified by chromatography on silica gel eluting with hexane and then with hexane/ethyl acetate 9/1. The fractions with the product were collected, concentrated and dried under high vacuum to yield 3. 8 G (25'M)) N-TERT-BUTYL-6-CHLORO-4-(4-FLUORO-2-METHYL-PHENYL)- nicotinamide as a light beige powder. MS (ISP) : m/e = 321 (M+H-', 36), 273 (M-TBU, 100).
  • 3
  • [ 50820-65-0 ]
  • [ 452-63-1 ]
  • [ 1609966-99-5 ]
YieldReaction ConditionsOperation in experiment
46% With potassium phosphate; copper(l) iodide; dodecane; rac-diaminocyclohexane; In 1,4-dioxane; at 110℃; for 8h; 1H-<strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> (200mg, 1.14mmol) was dissolved in dioxane (2ml). 1-Bromo-4-fluoro-2-methyl-benzene (0.3ml, 2.28mmol), copper (I) iodide (22mg, 0.11mmol), potassium phosphate tribasic (K3PO4, 509mg, 2.40mmol), dodecane (0.2ml, 0.11mmol) and cyclohexane 1,2-diamine (0.03ml, 0.23mmol) were added dropwise thereto, and then the mixture was stirred for 8 hours at 110. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (150mg, 46%).
 

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