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[ CAS No. 1147871-74-6 ]

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Chemical Structure| 1147871-74-6
Chemical Structure| 1147871-74-6
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Product Details of [ 1147871-74-6 ]

CAS No. :1147871-74-6 MDL No. :MFCD14584729
Formula : C10H10BrFO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :245.09 g/mol Pubchem ID :46941302
Synonyms :

Safety of [ 1147871-74-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1147871-74-6 ]

  • Downstream synthetic route of [ 1147871-74-6 ]

[ 1147871-74-6 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 1435-51-4 ]
  • [ 79-30-1 ]
  • [ 1147871-74-6 ]
YieldReaction ConditionsOperation in experiment
To a 50 L round bottomed flask fitted with a thermocouple and 5 L addition funnel, under a nitrogen atmosphere, was added ZnCl2 (32.7 g, 0.24 mol) and CuCl (23.3 g, 0.24 mol). THF (12 L) was added and the solution degassed by bubbling N2 through the slurry for 5 minutes. Following this 2,3-dibromofluorobenzene 11 (6.0 kg, 24 mol) was added in one portion. The reaction was cooled to 10 0C and isopropyl magnesium chloride (2 M, 14 L, 28 mol) was added dropwise over 1 hour 20 minutes while maintaining the temperature between 15 - 20 0C. A 100 L cylindrical vessel was charged with isobutyryl chloride (3.3 kg, 31 mol) and THF (6 L). The mixture was cooled to 6 0C before pumping previously prepared aryl Grignard solution into it over a 70 minute time period while maintaining the temperature between 10 0C - 18 0C. After complete addition, the reaction was aged for 20 minutes before being assayed for conversion. Upon complete conversion, the reaction was diluted with toluene (11 L) and IN citric acid (10 L). The bi-phasic mixture was stirred for 10 minutes before separating the layers. The organic layer was then treated with IN citric acid (10 L) and stirred for an additional 10 minutes. The layers were separated and the organic layer was washed sequentially with IN K2HPO4 (2 x 11 L) and water (11 L). The wet toluene batch was then held for 36 hours while a second batch of equal size was processed. The wet toluene batches containing isopropyl ketone 12 were then combined and concentrated to approximately 2-3 volumes and the KF < 200 ppm and were used directly in the next step. HPLC retention time of isopropyl ketone 12 = 8.1 min on 25 cm Zorbax SB C- 18, using MeCN / 0.1 H3PO4, 1 mL / min. gradient elution: 70% MeCN for 5 minutes then to 90% MeCN at 10 minutes; 210 nm; hold for 5 minutes. 1H NMR (400 MHz, CDCl3) delta 7.85 (IH, br. s, Ar-H), 7.56 <n="38"/>(IH, dd, 8.9 Hz, 1.0 Hz, Ar-H), 7.43 (IH, dd, 8 Hz, 1.0 Hz, Ar-H), 3.43 (IH, sep. 6.9 Hz, C-H), 1.21 (6H, d, 6.9 Hz, (CHj)2CH).
  • 2
  • [ 1147871-74-6 ]
  • [ 1147871-75-7 ]
YieldReaction ConditionsOperation in experiment
To a 100 L round bottomed flask fitted with a thermocouple, under an atmosphere of N2 was added sequentially sodium amylate (3.0 kg, 27.3 mol) and DMF (11 L). The slurry was aged for 30 minutes until almost all of the base had dissolved. Then the solution was cooled to 10 0C and a ~50 weight % solution of the isopropyl ketone 12 (10.8 kg, 50 weight %, 5.4 kg, 22 mol) was added over 55 minutes while maintaining the temperature between 15 - 20 0C via the controlled addition of the isopropyl ketone. Upon complete addition, the solution was aged for 30 minutes, cooled to 10 0C and treated with TBSCl (4.3 kg, 28.5 mol) over a 30 minute period while maintaining the temperature between 20 - 28 0C via controlled TBSCl addition. The reaction was aged for 30 minutes, then Select-Fluor (8.5 kg, 24 mol, Air Products) was then added over 1.5 hours while maintaining the reaction temperature 28 - 35 0C and the slurry aged for 1 hour. On complete conversion, water (18 L) was added, followed by toluene (12 L). The resulting biphasic mixture was transferred to a 100 L cylindrical vessel and aged for 10 minutes. The layers were separated and the organic phase was washed with additional water (9 L). The wet toluene solution containing fluoro ketone 13 was held for 36 hours while a second batch of equal size was processed. The combined toluene batches containing fluoro ketone 13 were then concentrated until the KF < 200 ppm and about 50 weight %. The resulting toluene solution of fluoro ketone 13 was used directly in the next step. HPLC retention time fluoro ketone 13 = 8.5 minutes on 25 cm Zorbax SB C-18, using MeCN / 0.1 H3PO4, 1 mL / min. gradient elution: 70% MeCN for 5 minutes, then to 90% MeCN at 10 minutes, hold for 5 minutes at 210 nm.IR vmax / cm"1 3083 (C-H), 2989 (C-H), 2941 (C-H), 1696 (C=O), 1577 (C=C); 1H NMR (500 MHz, CDCl3) delta 8.02 (IH, s, ArH), 7.74 (IH, br d, J^ = 9.1 Hz, ArH), 7.65 (IH, dt, 3HF = 7.66 Hz, JH.H = 2.0 Hz, ArH), 1.69 (6H, d, 3H.F = 21.7 Hz, 2 x CH3); 13C NMR (125 MHz, CDCl3) delta 198.2 (dd, J = 27.1 Hz, 1.8 Hz, C=O), 162.2 (d, J = 252.3 Hz, ArCF), 136.9 (dd, J = 6.8, 4.3 Hz, ArCCO), 128.9 (dd, J = 8.6, 3.1Hz, ArCH), 123.5 (d, J = 24.6 Hz, ArCH), 122.8 (dd, J = 9.2, 1.2 Hz, ArCBr), 115.8 (dd, J = 22.8, 9.2 Hz, ArCH), 99.9 (d, J = 180.3 Hz, C(CH3)2), 25.5 (d, J = 24.0 Hz, 2 x CH3); 19F NMR (470 MHz, CDCl3) delta -109.96, Ar-F), -144.68 (C-F).
  • 3
  • [ 110-91-8 ]
  • [ 1147871-74-6 ]
  • 1-[3-fluoro-5-(morpholin-4-yl)phenyl]-2-methylpropan-1-one [ No CAS ]
  • 4
  • [ 1435-51-4 ]
  • [ 113778-69-1 ]
  • [ 1147871-74-6 ]
  • 5
  • [ 1147871-74-6 ]
  • {1-[3-fluoro-5-(morpholin-4-yl)phenyl]-2-methylpropylidene}propanedinitrile [ No CAS ]
  • 6
  • [ 1147871-74-6 ]
  • (±)-6-amino-4-[3-fluoro-5-(morpholin-4-yl)phenyl]-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile [ No CAS ]
  • 7
  • [ 1147871-74-6 ]
  • benzyl 3'-fluoro-5'-(2-methylpropanoyl)[1,1'-biphenyl]-3-carboxylate [ No CAS ]
  • 8
  • [ 1147871-74-6 ]
  • benzyl [3'-fluoro-5'-(2-methylpropanoyl)[1,1'-biphenyl]-3-yl]acetate [ No CAS ]
  • 9
  • [ 1147871-74-6 ]
  • benzyl 3-[3'-fluoro-5'-(2-methylpropanoyl)[1,1'-biphenyl]-3-yl]propanoate [ No CAS ]
  • 10
  • [ 1147871-74-6 ]
  • benzyl 3'-(1,1-dicyano-3-methylbut-1-en-2-yl)-5'-fluoro[1,1'-biphenyl]-3-carboxylate [ No CAS ]
  • 11
  • [ 1147871-74-6 ]
  • benzyl [3'-(1,1-dicyano-3-methylbut-1-en-2-yl)-5'-fluoro[1,1'-biphenyl]-3-yl]acetate [ No CAS ]
  • 12
  • [ 1147871-74-6 ]
  • benzyl 3-[3'-(1,1-dicyano-3-methylbut-1-en-2-yl)-5'-fluoro[1,1'-biphenyl]-3-yl]propanoate [ No CAS ]
  • 13
  • [ 1147871-74-6 ]
  • (±)-benzyl 3'-[6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5'-fluoro[1,1'-biphenyl]-3-carboxylate [ No CAS ]
  • 14
  • [ 1147871-74-6 ]
  • (±)-benzyl {3'-[6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5'-fluoro[1,1'-biphenyl]-3-yl}acetate [ No CAS ]
  • 15
  • [ 1147871-74-6 ]
  • (±)-benzyl 3-{3'-[6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5'-fluoro[1,1'-biphenyl]-3-yl}propanoate [ No CAS ]
  • 16
  • [ 1147871-74-6 ]
  • (±)-3'-[6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5'-fluoro[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
  • 17
  • [ 1147871-74-6 ]
  • benzyl 1-[3-(1,1-dicyano-3-methylbut-1-en-2-yl)-5-fluorophenyl]piperidine-4-carboxylate [ No CAS ]
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