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Chemical Structure| 915412-18-9 Chemical Structure| 915412-18-9

Structure of 915412-18-9

Chemical Structure| 915412-18-9

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Product Details of [ 915412-18-9 ]

CAS No. :915412-18-9
Formula : C7H6BrIO
M.W : 312.93
SMILES Code : COC1=CC(I)=CC(Br)=C1
MDL No. :MFCD12547766

Safety of [ 915412-18-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 915412-18-9 ]

* 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 [ 915412-18-9 ]

[ 915412-18-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 16618-68-1 ]
  • [ 915412-18-9 ]
  • 2
  • [ 74137-36-3 ]
  • [ 915412-18-9 ]
YieldReaction ConditionsOperation in experiment
60% A 1.6 M solution of n-butyllithium in hexane (5.65 mL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5° C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL, 4.52 mmol) was added slowly with the temperature held below 0° C. over a period of 15 min. Stirring was continued for 45 min at -5° C., followed by drop wise addition of a solution of 1,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 0° C. The mixture was stirred for 45 min at -5° C. A solution of iodine chloride (1.83 g, 11.3 mmol) in methylene chloride (20 mL) was added in the described manner and stirring continued for additional 20 min at -5° C. The mixture was warmed to room temperature. Water (50 mL) and toluene (50 mL) were added and the layers were separated. The organic layer was washed with a saturated aqueous solution of Na2S2O3 (2.x.30 mL), water and brine (30 mL). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (100 g, AcOEt/heptane 1:9). 1-Bromo-3-iodo-5-methoxy-benzene (2.12 g, 60percent) was obtained as a yellow oil, which crystallized quickly upon standing.
60% 1-Bromo-3-iodo-5-methoxy-benzeneA 1.6 M solution of n-butyllithium in hexane (5.65 mL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5° C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL, 4.52 mmol) was added slowly with the temperature held below 0° C. over a period of 15 min. Stirring was continued for 45 min at -5° C., followed by drop wise addition of a solution of 1,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 0° C. The mixture was stirred for 45 min at -5° C. A solution of iodine chloride (1.83 g, 11.3 mmol) in methylene chloride (20 mL) was added in the described manner and stirring continued for additional 20 min at -5° C. The mixture was warmed to room temperature. Water (50 mL) and toluene (50 mL) were added and the layers were separated. The organic layer was washed with a saturated aqueous solution of Na2S2O3 (2.x.30 mL), water and brine (30 mL). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (100 g, AcOEt/heptane 1:9). 1-Bromo-3-iodo-5-methoxy-benzene (2.12 g, 60percent) was obtained as a yellow oil, which crystallized quickly upon standing.
60% [0353] A 1.6 M solution of n-butyllithium in hexane (5.65 niL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5°C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL , 4.52 mmol) was added slowly with the temperature held below 0°C over a period of 15 min. Stirring was continued for 45 min at -5°C, followed by drop wise addition of a solution of l,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 00C. The mixture was stirred for 45 min at -5°C. A solution of iodine chloride (1.83 g, 11.3 mmol) in methylene chloride (20 mL) was added in the described manner and stirring continued for additional 20 min at -5°C. The mixture was warmed to room temperature. Water (50 mL) and toluene (50 mL) were added and the layers were separated. The organic layer was washed with a saturated aqueous solution OfNa2S2O3 (2 x 30 mL), water and brine (30 mL). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (100 g, AcOEt/heptane 1:9). l-Bromo-3-iodo-5- methoxy-benzene (2.12 g, 60 percent) was obtained as a yellow oil, which crystallized quickly upon standing.
  • 3
  • [ 915412-18-9 ]
  • [ 570391-20-7 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogen bromide; acetic acid;tetrabutylammomium bromide; for 48h;Heating / reflux; 1-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33percent, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted with methylene chloride (3.x.100 mL). The combined organic layers were washed with water (50 mL), dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9). 3-Bromo-5-iodo-phenol (21.2 g, 96percent) was obtained as pale brown solid.
96% With tetrabutylammomium bromide; hydrogen bromide; acetic acid; for 48h;Heating / reflux; 3-Bromo-5-iodo-phenol1-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33percent, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted with methylene chloride (3.x.100 mL). The combined organic layers were washed with water (50 mL), dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9). 3-Bromo-5-iodo-phenol (21.2 g, 96percent) was obtained as pale brown solid.
96% With tetrabutylammomium bromide; hydrogen bromide; In acetic acid; for 48h;Heating / reflux; [0355] l-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33 percent, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted with methylene chloride (3 x 100 mL). The combined organic layers were washed with water (50 mL), dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9). 3-Bromo-5-iodo- phenol (21.2 g, 96 percent) was obtained as pale brown solid.
 

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