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[ CAS No. 1125828-26-3 ]

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2D
Chemical Structure| 1125828-26-3
Chemical Structure| 1125828-26-3
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Product Details of [ 1125828-26-3 ]

CAS No. :1125828-26-3MDL No. :MFCD14706004
Formula : C10H8BrClN2 Boiling Point : 344.8±37.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :QYIGOGBGVKONDY-UHFFFAOYSA-N
M.W :271.54Pubchem ID :25212417
Synonyms :

Computed Properties of [ 1125828-26-3 ]

TPSA : 17.8 H-Bond Acceptor Count : 1
XLogP3 : 3.6 H-Bond Donor Count : 0
SP3 : 0.10 Rotatable Bond Count : 1

Safety of [ 1125828-26-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1125828-26-3 ]

  • Upstream synthesis route of [ 1125828-26-3 ]
  • Downstream synthetic route of [ 1125828-26-3 ]

[ 1125828-26-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 1453-58-3 ]
  • [ 1996-29-8 ]
  • [ 1125828-26-3 ]
  • [ 1125828-28-5 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 0.25 h;
Stage #2: at 50℃; for 5.00 h;
A 3L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95percent, 84.6 g, 0.716 mol) and DMSO (400 mL, 4.x.) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5.x.). The resulting orange turbid solution was stirred for 15 minutes and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5.x.). This mixture was then heated to 50° C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 minutes stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99percent, solution yields of 3 and its regioisomer 4 were 83percent and 17percent, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737percent water). THF (500 mL) was added, and concentrated to 2.x. solution (KF=0.158percent). THF addition-concentration sequence was repeated to give a 2.x. solution (KF=0.023percent), which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; M.p.: 76° C. (DSC onset temperature). 1H NMR (400 MHz, CDCl3) δ 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); 13C NMR (100 MHz, CDCl3) δ 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; 1H NMR (400 MHz, CDCl3) δ 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); 13C NMR (100 MHz, CDCl3) δ 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.
83 %Chromat.
Stage #1: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 0.25 h;
Stage #2: at 50℃; for 5.00 h;
.1. Preparation of 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone A 3 L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95percent, 84.6 g, 0.716 mol) and DMSO (400 mL, 4.x.) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5.x.). The resulting orange turbid solution was stirred for 15 min and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5.x.). This mixture was then heated to 50° C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 min stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99percent, solution yields of 3 and its regioisomer 4 were 83percent and 17percent, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737percent water). THF (500 mL) was added, concentrated to 2.x. solution (KF=0.158percent). THF addition-concentration sequence was repeated to give a 2.x. solution (KF=0.023percent) which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; 1H NMR (400 MHz, CDCl3) δ 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); 13C NMR (100 MHz, CDCl3) δ 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; 1H NMR (400 MHz, CDCl3) δ 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); 13C NMR (100 MHz, CDCl3) δ 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.
Reference: [1] Patent: US2009/62540, 2009, A1. Location in patent: Page/Page column 6-7
[2] Patent: US2009/88447, 2009, A1. Location in patent: Page/Page column 4
[3] Patent: WO2015/35113, 2015, A1. Location in patent: Page/Page column 71
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