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[ CAS No. 921630-14-0 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 921630-14-0
Chemical Structure| 921630-14-0
Structure of 921630-14-0 *Storage: {[proInfo.prStorage]}

Quality Control of [ 921630-14-0 ]

Related Doc. of [ 921630-14-0 ]

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Alternatived Products of [ 921630-14-0 ]
Alternatived Products of [ 921630-14-0 ]

Product Details of [ 921630-14-0 ]

CAS No. :921630-14-0MDL No. :MFCD09907898
Formula : C6H3BrClNO Boiling Point : 281.9±35.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :220.45Pubchem ID :-
Synonyms :

Computed Properties of [ 921630-14-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 921630-14-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 921630-14-0 ]

  • Downstream synthetic route of [ 921630-14-0 ]

[ 921630-14-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 40473-01-6 ]
  • [ 68-12-2 ]
  • [ 921630-14-0 ]
YieldReaction ConditionsOperation in experiment
72% To a stirred sol. of diisopropylamine (20.9 mL, 148 mmol) in dry THF (350 mL) at -5 C. was added dropwise BuLi (1.6M in hexane, 89.5 mL, 143 mmol), and the resulting sol. was stirred for 30 min at -5 C. The sol. was allowed to cool to -70 C., and a sol. of <strong>[40473-01-6]2-bromo-5-chloropyridine</strong> (25.0 g, 130 mmol) in THF (100 mL) was added dropwise at -70 C. over 15 min such that the internal temperature did not exceed -65 C. The mixture was stirred at -70 C. for 30 min. DMF (10.52 mL, 136 mmol) was added dropwise over 20 min such that the internal temperature did not exceed -70 C. The orange mixture was stirred at -70 C. for 40 min. The mixture was allowed to warm up to rt, and was poured onto a mixture of water (200 mL) and aq. 1M NaOH (50 mL). The mixture was extracted with EtOAc (2×), and the combined org. extracts were washed back with aq. 1M NaOH (2×). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:9?1:8?1:6?1:4?1:2?1:1) yielded the title compound (21.55 g, 72%). LC-MS: tR=0.74 min; ES+: 295.01.
72% To a stirred sol. of diisopropylamine (20.9 mL, 148 mmol) in dry THF (350 mL) at -5 C. was added dropwise BuLi (1.6M in hexane, 89.5 mL, 143 mmol), and the resulting sol. was stirred for 30 min at -5 C. The sol. was allowed to cool to -70 C., and a sol. of <strong>[40473-01-6]2-bromo-5-chloropyridine</strong> (25.0 g, 130 mmol) in THF (100 mL) was added dropwise at -70 C. over 15 min, such that the internal temperature did not exceed -65 C. The mixture was stirred at -70 C. for 30 min. DMF (10.52 mL, 136 mmol) was added dropwise over 20 min such that the internal temperature did not exceed -70 C. The orange mixture was stirred at -70 C. for 40 min. The mixture was allowed to warm up to rt, and was poured onto a mixture of water (200 mL) and aq. 1M NaOH (50 mL). The mixture was extracted with EtOAc (2×), and the combined org. extracts were washed back with aq. 1M NaOH (2×). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:9?1:8?1:6?1:4?1:2?1:1) yielded the title compound (21.55 g, 72%). LC-MS: tR=0.74 min; ES+: 295.01.
72% <strong>[40473-01-6]2-Bromo-5-chloro-pyridine</strong>-4-carbaldehyde To a stirred sol. of diisopropylamine (20.9 mL, 148 mmol) in dry THF (350 mL) at -5 C. was added dropwise BuLi (1.6M in hexane, 89.5 mL, 143 mmol), and the resulting sol. was stirred for 30 min at -5 C. The sol. was allowed to cool to -70 C., and a sol. of <strong>[40473-01-6]2-bromo-5-chloropyridine</strong> (25.0 g, 130 mmol) in THF (100 mL) was added dropwise at -70 C. over 15 min such as the internal temperature did not exceed -65 C. The mixture was stirred at -70 C. for 30 min. DMF (10.5 mL, 136 mmol) was added dropwise over 20 min at such a rate that the internal temperature did not exceed -70 C. The orange mixture was stirred at -70 C. for 40 min. The mixture was allowed to warm up to rt, and was poured onto a mixture of water (200 mL) and aq. 1M NaOH (50 mL). The mixture was extracted with EtOAc (2*), and the combined org. extracts were washed back with aq. 1M NaOH (2*). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:9?1:8?1:6?1:4?1:2?1:1) yielded the title compound (21.6 g, 72%). LC-MS: tR=0.74 min; ES+: 295.01.
72% <strong>[40473-01-6]2-Bromo-5-chloro-pyridine</strong>-4-carbaldehyde. To a stirred sol. of diisopropylamine (20.9 mL, 148 mmol) in dry THF (350 mL) at -5 0C was added dropwise BuLi (1.6M in hexane, 89.5 mL, 143 mmol), and the resulting sol. was stirred for 30 min at -5 0C. The sol. was allowed to cool to -70 0C, and a sol. of 2- bromo-5-chloropyridine (25.0 g, 130 mmol) in THF ( 100 mL) was added dropwise at -70 0C over 15 min such as the internal temperature did not exceed -65 0C. The mixture was stirred at -70 0C for 30 min. DMF (10.5 mL, 136 mmol) was added dropwise over 20 min <n="46"/>at such a rate that the internal temperature did not exceed -70 0C. The orange mixture was stirred at -70 0C for 40 min. The mixture was allowed to warm up to rt, and was poured onto a mixture of water (200 mL) and aq. IM NaOH (50 mL). The mixture was extracted with EtOAc (2x), and the combined org. extracts were washed back with aq. IM NaOH (2x). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtO Ac/heptane 1 :9 - > 1 :8 - > 1 :6 ? 1 :4 ? 1 :2 ? 1 :1) yielded the title compound (21.6 g, 72 %). LC-MS: tR = 0.74 min; ES+: 295.01.

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