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CAS No. : | 187283-17-6 | MDL No. : | MFCD11974929 |
Formula : | C13H18BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UYGBIHFTZHBDEQ-UHFFFAOYSA-N |
M.W : | 300.19 | Pubchem ID : | 23447255 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 | UN#: | 3261 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With phosphorus tribromide; In tetrahydrofuran; at -78℃; for 2h; | A solution of 4-(N-t-Boc-aminomethyl)benzyl alcohol (250 mg, 1.1 mmol) in THF (5 mL) was treated with phosphorustribromide (30 uL, 0.32 mmol) at -78° C. for 2 h. After this period, the reaction was quenched with solid NaHCO3 (50 mg) and filtered to remove the solids and the filtrate was evaporated to give 4-(t-Boc-aminomethyl)benzyl bromide (300 mg, 95percent). |
32% | With pyridine; N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 16h; | N-Bromosuccinimide (5.13 g, 28.8 mmol) was dissolved in DCM (80 mL) and cooled to 0 0C. A solution of triphenylphosphine (7.18 g, 27.0 mmol) in DCM (20 mL) was prepared and added to the chilled solution followed by pyridine (1.0 mL, 1.26 mmol). Material from step 2 (2.14 g, 9.0 mmol) was dissolved in DCM (20 mL) and added and the reaction allowed to warm to r.t. and stirred for 16 h. The mixture was concentrated and the residue purified by column chromatography (50percent/50percent EtOAc/heptane) to afford the desired compound (864 mg, 32percent). m/z 301 [M++Na]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | General procedure: 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 × 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74%) as orange red crystals. |
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