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Chemistry
Organometallic Reagents
Organoboron
2-(4-Bromo-2,3-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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[ CAS No. 2121511-55-3 ] {[proInfo.proName]}

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Chemical Structure| 2121511-55-3
Chemical Structure| 2121511-55-3
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Quality Control of [ 2121511-55-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 2121511-55-3 ]

CAS No. :2121511-55-3 MDL No. :MFCD29036581
Formula : C14H20BBrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 311.02 Pubchem ID :-
Synonyms :

Safety of [ 2121511-55-3 ]

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

Application In Synthesis of [ 2121511-55-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2121511-55-3 ]

[ 2121511-55-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 61676-62-8 ]
  • [ 1160573-43-2 ]
  • [ 2121511-55-3 ]
YieldReaction ConditionsOperation in experiment
63.6% Stage #1: 1-bromo-4-iodo-2,3-dimethylbenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - -10℃; for 1.5h; 15.1 Step 1 : 2-(4-bromo-2,3-dimethylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane To a solution containing l-bromo-4-iodo-2,3-dimethylbenzene (975 mg, 3.14 mmol) in THF (20 mL), cooled to -78 °C in a dry ice acetone bath, was added dropwise BuLi (1.380 mL, 3.45 mmol). The reaction mixture was stirred for 30 min and 2- isopropoxy-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.768 mL, 3.76 mmol) was added dropwise. The reaction mixture was stirred for an additional 30 min at -78 °C and warmed to approximately -10 °C for 1 h. The reaction mixture was quenched with saturated ammonium chloride (5 mL). The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (2 X 20 mL) and sat. aq. NaCl solution (1 X 20 mL), dried (Na2S04), filtered and concentrated. The crude product was dissolved in a small amount of DCM and charged to 24 g ISCO silica gel Column and purified using the Teledyne ISCO system, eluting over a 15 min gradient with 0%-30% hexanes/ethyl acetate to obtain 2-(4-bromo-2,3-dimethylphenyl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane (15B) (620 mg, 1.993 mmol, 63.6% yield. NMR (400 MHz, CHLOROFORM-d) d 7.48-7.38 (m, 1H), 7.30-7.27 (m, 1H), 2.56 (s, 3H), 2.41 (s, 3H), 1.37 (s, 12H).
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2021/67657, 2021, A1 Location in patent: Page/Page column 63

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