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[ CAS No. 251115-21-6 ]

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Chemical Structure| 251115-21-6
Chemical Structure| 251115-21-6
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CAS No. :251115-21-6 MDL No. :MFCD11226284
Formula : C7H3BrF3NO2 Boiling Point : 268.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :270.00 g/mol Pubchem ID :18371261
Synonyms :

Safety of [ 251115-21-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 251115-21-6 ]

  • Upstream synthesis route of [ 251115-21-6 ]
  • Downstream synthetic route of [ 251115-21-6 ]

[ 251115-21-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 251115-21-6 ]
  • [ 703-91-3 ]
YieldReaction ConditionsOperation in experiment
90% With iron; ammonium chloride In tetrahydrofuran; ethanol; water at 80℃; for 1 h; To a suspension of 4-bromo-2-nitro- 1 -(trifluoromethyl)benzene (4.0 g, 14.9mmol) in ethanol (23OmL), THF (85mL), and water (4OmL) was added ammonium chloride (1.0 g, 18.8mmol) and ferrous powder (5.06 g, 90mmol). The resulting mixture was heated at 80 0C for 1 hr and the progress of the reaction was monitored by TLC. Upon complete consumption of staring material, the reaction mixture was filtered off while it was hot. The filtrate was evaporated under vacuum and the crude residue was diluted with ethyl acetate (10OmL) and washed with water (3 x 5OmL). The combined organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum to afford 5-bromo-2-(trifluoromethyl)aniline as a solid (3.2g, 90percent).
79% at 0 - 20℃; for 2 h; 5-bromo-2-(trifluoromethyl)aniline (1) : To a solution of 4-bromo-2-nitro-l- (trifluoromethyl)benzene (2.0 g, 7.4 mmol) in acetic acid (10.0 mL), Iron powder (1.2 g, 21.8 mmol) was added at 0 °C. The resulting reaction mixture was stirred at room temperature for 2 h. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with water, basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2x50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 1 (1.4 g, 79percent) as a brown gummy solid. 1H NMR (400 MHz, DMSO-d6): δ 5.86 (brs, 2H), 6.73-6.73 (dd, J = 1.2, 8.4 Hz, 1H), 7.02 (s, 1H), 7.23-7.25 (d, J = 8.4 Hz, 1H). MS m/z (M+H): 240.1
Reference: [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 100
[2] Patent: WO2014/149164, 2014, A1, . Location in patent: Paragraph 00763; 00895
  • 2
  • [ 680-15-9 ]
  • [ 3460-18-2 ]
  • [ 251115-21-6 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃; To a solution of 1, 4-dibromo-2-nitrobenzene (5 g, 17.8mmol) in N- methylpyrrolidinone (4OmL) were added methyl difluoro(fluorosulfonyl)acetate (4.5mL, 35.6mmol) and copper(l) iodide. The mixture was heated at 80 0C overnight, decolorized with activated charcoal, diluted with brine and extracted with ethyl acetate (3X3OmL). The combined extracts was dried over MgSO4, concentrated in vacuum and purified by flash chromatography (0-lOOpercent ethyl acetate in petroleum) to give 4-bromo-2-nitro-l-(trifluoromethyl)benzene (4.1 g, 85percent) as a yellow oil.
85% With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃; b) 4-Bromo-2-nitro-1 -(trif luoromethyl)benzeneTo a solution of 1 ,4-dibromo-2-nitrobenzene (5 g, 17.8 mmol) in N- methylpyrrolidinone (40 mL) were added methyl difluoro(fluorosulfonyl)acetate (4.5 mL, 35.6 mmol) and copper(l) iodide. The mixture was heated at 80 0C overnight, decolorized with activated charecoal, diluted with brine and extracted with ethyl acetate (3 x 30 mL). The combined extracts was dried over MgSOφ concentrated in EPO <DP n="69"/>vacuo and purified by flash chromatography (0-100percent ethyl acetate in hexanes) to give the title compound (4.1 g, 85percent) as a yellow oil. 1 H NMR (400MHz, CDCI3) δ8.15 (s, 1 H), 7.90 (d, J = 8.1 Hz, 1 H), 7.75 (d, J = 8.1 Hz, 1 H).
85% With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃; for 24 h; PREPARATION 45 3-fluoro-3'-nitro-4'-(trifluoromethyl)-4-biphenylamine To a solution of 1,4-dibromo-2-nitrobenzene (5.0 g, 17.8 mMol) in 1-methyl-2-pyrrolidinone (25 mL) was added copper(I) iodide (0.85 g, 4.5 mMol) and methyl 2-(fluorosulfonyl)difluoroacetate (4.6 mL, 36.1 mMol). The reaction mixture was heated at 80° C. for 24 h. After cooling to room temperature, the reaction mixture was diluted with water and the organics were extracted with ethyl acetate, filtered to remove insolubles, washed with brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by silica gel chromatography (5percent ethyl acetate/hexanes) gave the intermediate 4-bromo-2-nitro-1-(trifluoromethyl)benzene (4.10 g, 85percent) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.06 (d, 1H, J=1.5 Hz), 7.87-7.92 (m, 1H), 7.73 (d, 1H, J=8.3 Hz).
Reference: [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 100
[2] Patent: WO2006/113432, 2006, A2, . Location in patent: Page/Page column 67-68; 37
[3] Patent: US2007/142460, 2007, A1, . Location in patent: Page/Page column 18
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