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Chemistry
Heterocyclic Building Blocks
Benzodioxans
6-(Bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Benzodioxans
Bromides

[ CAS No. 79440-34-9 ] {[proInfo.proName]}

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Chemical Structure| 79440-34-9
Chemical Structure| 79440-34-9
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Product Details of [ 79440-34-9 ]

CAS No. :79440-34-9 MDL No. :MFCD02681901
Formula : C9H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 229.07 Pubchem ID :-
Synonyms :

Safety of [ 79440-34-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 79440-34-9 ]

* 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 [ 79440-34-9 ]

[ 79440-34-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 39270-39-8 ]
  • [ 79440-34-9 ]
YieldReaction ConditionsOperation in experiment
84% With phosphorus tribromide; In dichloromethane; at 0℃; for 0.5h; To a solution of (2,3- dihydrobenzo[b][l,4]dioxin-6-yl)methanol (2.77 g, 16.66 mmol) in CH2CI2 was added PBn (0.63 mL, 6.66 mmol) dropwise at 0 C. The mixture was stirred at 0 C for 0.5 h. Upon completion, the mixture was diluted with CH2CI2 and washed with saturated NaHCCL. The organic layer was concentrated under vacuum. Colorless oil (hexanes :ethyl acetate = 20:1, 3.22 g, 84% yield) was isolated with column chromatography. 1 H NMR (500 MHz, Chlorol'ornw/) d 6.92 (d, J = 3.1 Hz, 1H), 6.88 (dd, J = 8.4, 2.5 Hz, 1H), 6.82 (dt, J = 8.4, 2.4 Hz, 1H), 4.44 (d, J = 2.0 Hz, 2H), 4.28 - 4.21 (m, 4H). 13C NMR (126 MHz, Chloroform-^/) d 143.82, 143.46, 130.93, 122.28, 118.02, 117.55, 64.39, 64.27, 33.82
80% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 24h; To a solution of (2,3-dihydrobenzo[b][l,4]dioxin-6-yl)methanol (1.0 g, 6.0 mmol) in dichloromethane (25 mL) was added carbontetrabromide (3.0 g, 9 mmol), and triphenylphosphine (2.35 g, 9.0 mmol). The reaction mixture was stirred at room temperature for 24 h and concentrated under reduced pressure. Purification by column chromatography (Silica gel, EtOAc/Hexanes) resulted in 1.1 g (80% Yield) of 6-(bromomethyl)-2,3- dihydrobenzo[b][l,4]dioxine. MS (EI) for C9H9BrO2 found 229 (MH+)
37% With phosphorus tribromide; In diethyl ether; at -40 - 20℃; 6-(Bromomethyl)-2,3-dihydrobenzo[b][l,4]dioxine. To a solution of(2,3-dihydrobenzo[b][l,4]dioxin-6-yl)methanol (46 g, 0.28 mol) in Et2O (1 L) at - 40 0C was added PBr3 (84 g, 0.3 mol, Aldrich) dropwise. The resulting mixture was stirred for 16 hoursat room temperature. The reaction was quenched by careful addition of H2O (1 L). The organic phase was separated, washed with H2O (2 x 1 L), dried (Na2SO4), filtered, and concentrated in vacuo to give the initial product, which was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (100: 1 to 20: 1) to afford 6-(bromomethyl)-2,3-dihydrobenzo[b][l,4]dioxine (23 g, 37 %).
With phosphorus tribromide; In dichloromethane; at 0℃; for 0.5h; General procedure: To a solution of phenylmethanols 5a-w (5 mmol) dissolved in methylene chloride (50 mL) in an ice-water bath was added phosphorus tribromide (5.5 mmol), and the mixture was stirred at the same temperature for 30 min. The mixture was washed with cool water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (bromomethyl)benzenes 6aew as offwhite solids or light yellow oils
With phosphorus tribromide; In dichloromethane; at 0 - 5℃; for 0.75h; General procedure: crude product 2a which was then dissolved in anhydrous methylene chloride (50 mL) and cooled to 0-5 ºC by ice bath. To this solution was added dropwise phosphorus tribromide (0.5 mL, 5 mmol) over a period of 15 min and stirred for 0.5 h at the same temperature, and then washed with saturated brine (3 Chi 15 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude compound 3a.
With boron tribromide; In dichloromethane; at 20℃; for 8h; Boron tribromide (2.6 g, 10 mmol) was slowly added to a solution of 1 (1.66 g, 10 mmol) in anhydrous dichloromethane (10 mL) and the mixture was stirred at room temperature for 8 h while monitoring by TLC. The mixture was then concentrated under reduced pressure and saturated sodium bicarbonate solution was added to pH 7. The product was obtained by precipitation.

Reference： [1]Patent: WO2019/191410,2019,A1 .Location in patent: Page/Page column 40
[2]Patent: WO2010/91104,2010,A1 .Location in patent: Page/Page column 51
[3]Patent: WO2010/83246,2010,A1 .Location in patent: Page/Page column 149-150
[4]Tetrahedron,2001,vol. 57,p. 8297 - 8303
[5]Journal of Medicinal Chemistry,2011,vol. 54,p. 1033 - 1058
[6]European Journal of Medicinal Chemistry,2012,vol. 55,p. 125 - 136
[7]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5971 - 5975
[8]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5626 - 5632
  • 2
  • [ 951122-37-5 ]
  • [ 79440-34-9 ]
  • C16H13F2NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.8% Potassium carbonate (362 mg, 2.62 mmol) was added to a solutionof <strong>[951122-37-5]2,6-difluoro-3-hydroxybenzamide</strong> (453 mg, 2.62 mmol) inDMF (3 mL). After stirring at room temperature for 15 min, a solutionof 1,2-ethylenedioxy-4-bromomethylbenzene (500 mg,2.18 mmol) in DMF (3 mL) was added. The reaction mixture wasstirred at 100 C for 1 h, cooled to room temperature and thenpoured into iced water (80 mL). A precipitate was formed which was collected by filtration, washed with water, dried under vacuumand crystallized from CHCl3 to give 426 mg (60.8%) of 8 as a palepink solid: mp 130.0 C; 1H NMR (DMSO-d) delta 8.11 (br s,1 H), 7.83 (brs, 1 H), 7.25 (dd, 1 H, J 9.2, 5.4 Hz), 7.03 (dd, 1 H, J 9.2, 1.7 Hz),6.88 (m, 3 H), 5.03 (s, 2 H), 4.22 (s, 4 H). 13C NMR (DMSO-d) delta 162.0,152.5 (dd, J 239.7, 6.8 Hz),148.7 (dd, J 247.0, 8.4 Hz),144.1,143.9,143.4 (dd, J 10.8, 3.1 Hz), 129.9, 121.8, 117.7 (d, J 4.3 Hz), 117.3,117.0, 116.4 (dd, J 9.4, 2.3 Hz), 111.5 (dd, J 23.0, 3.8 Hz), 71.1,64.73, 64.71. Anal. Calcd for C16H13F2NO4 (321.28).
Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 120,p. 227 - 243

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