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[ CAS No. 153505-37-4 ]

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Chemical Structure| 153505-37-4
Chemical Structure| 153505-37-4
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Product Details of [ 153505-37-4 ]

CAS No. :153505-37-4 MDL No. :MFCD08458150
Formula : C6H6BrFN2 Boiling Point : 297°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :205.03 g/mol Pubchem ID :19958560
Synonyms :

Safety of [ 153505-37-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153505-37-4 ]

  • Upstream synthesis route of [ 153505-37-4 ]
  • Downstream synthetic route of [ 153505-37-4 ]

[ 153505-37-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 153505-36-3 ]
  • [ 153505-37-4 ]
YieldReaction ConditionsOperation in experiment
82% With ammonium formate; zinc In methanol at 0 - 20℃; Inert atmosphere To a flask was added 5-fluoro-2-nitroaniline (8.9 g, 57 mmol), NBS (10 g, 56 mmol), and acetic acid (500 mL), and the reaction was heated to 110 °C.
Once complete it was cooled to room temperature and poured into 3 L of water.
The resulting suspension was filtered and the solid was washed with 500 mL of water.
Solid was air dried overnight (12.7 g, 91 percent).
1H NMR (400 MHz, DMSO-d6) δ 8.27 (d, J = 7.3 Hz, 1H), 7.73 (br. S., 2H), 6.94 (d, J = 11.0 Hz, 1H).
4-bromo-5-fluoro-2-nitroaniline (0.53 g, 2.255 mmol), zinc (0.89 g, 13.5 mmol), and methanol (32 ml) were added to the flask and argon was bubbled through the solution for 1 hour.
Ammonium formate (1.42 g, 22.6 mmol) was then added in several portions.
The reaction was then stirred at room temperature overnight and was complete by LCMS in the morning.
It was filtered through a pad of celite and the filtrate was concentrated.
The residue was partitioned between water and EtOAc and the organic layer was collected.
The aqueous layer was back-extracted using EtOAc (2 x 50 mL).
The combined organics were dried over sodium sulfate, filtered, and concentrated (378 mg, 82 percent). MS (m/z) 205.0, 207.0 (M+, M+2+).
81% With iron; ammonium chloride In tetrahydrofuran; ethanol; water at 95℃; for 4 h; Intermediate 11C; 4-bromo-5 -fluorobenzene- 1 ,2-diamine; To a solution of 4-bromo-5-fluoro-2-nitroaniline (1.0 g, 4.3 mmol) in THF (9.0 mL), EtOH (9.0 mL) and H20 (3 mL) was added iron powder (1.2 g, 21.3 mmol) and ammonium chloride (0.34 g, 6.4 mmol), and the mixture was heated at 95 °C for 4 hours. The cooled mixture was diluted with EtOH, filtered through diatomaceous earth until no further color came through the filter, and concentrated. The residue was dissolved in EtOAc, washed with H20, brine, dried (Na2S04), filtered and concentrated. Hexane was added and the resulting solid collected by filtration to give the title compound (710 mg, 3.5 mmol, 81percent).
43% With tin(ll) chloride In ethanol for 14 h; Reflux step 2: To a suspension of 96 (1.57 g, 6.74 mmol) in EtOH (16 mL) was added SnC¾ (3.82 g, 20.2 mmol). The reaction mixture was heated at reflux for 14 h, cooled to RT and concentrated in vacuo. The residue was partitioned between EtOAc (100 mL) and sat'd. aq. NaHCC>3 (200 mL). The resulting slurry was filtered through a pad of Celite® and the wet cake was washed with EtOAc (3 x 50 mL). The organic layer was washed sequentially with saturated NaHC03, water, and brine, dried (MgSO i), filtered and concentrated in vacuo to afford 600 mg (43percent) of 44oromo-5-fluorobenzene-l,2-diamine (98) as yellow solid: MS (ESI) m/z = 205 [M+l]
Reference: [1] Patent: EP2566477, 2015, B1, . Location in patent: Paragraph 0172; 0173
[2] Patent: WO2012/83170, 2012, A1, . Location in patent: Page/Page column 155
[3] Patent: WO2013/26914, 2013, A1, . Location in patent: Page/Page column 134
[4] Patent: US2007/259936, 2007, A1, . Location in patent: Page/Page column 175
[5] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 69
  • 2
  • [ 153505-36-3 ]
  • [ 153505-37-4 ]
Reference: [1] Patent: US5514680, 1996, A,
  • 3
  • [ 2369-11-1 ]
  • [ 153505-37-4 ]
Reference: [1] Patent: WO2013/26914, 2013, A1,
[2] Patent: EP2566477, 2015, B1,
[3] Patent: US5514680, 1996, A,
  • 4
  • [ 656-65-5 ]
  • [ 153505-37-4 ]
Reference: [1] Patent: WO2012/83170, 2012, A1,
  • 5
  • [ 929279-27-6 ]
  • [ 153505-37-4 ]
Reference: [1] Patent: WO2012/83170, 2012, A1,
  • 6
  • [ 64-18-6 ]
  • [ 153505-37-4 ]
  • [ 1008360-84-6 ]
YieldReaction ConditionsOperation in experiment
87% Reflux step 3: A mixture of 98 (600 mg, 2.93 mmol) in formic acid (5.0 mL) was heated to reflux overnight. The reaction mixture was concentrated in vacuo to afford a brown oil that was partitioned between EtOAc (300 mL) and a sat'd. aq. NaHC03 (100 mL). The organic layer was separated, dried (MgSO i), filtered and evaporated in vacuo to afford 550 mg (87percent) of 54oromo-6-fluoro-lH4oenzo[d]imidazole (100) as white solid (550 mg, 87percent): MS (ESI) m/z = 215 [M+l] +.
Reference: [1] Patent: WO2013/26914, 2013, A1, . Location in patent: Page/Page column 134
[2] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 70
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