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Chemical Structure| 115467-08-8 Chemical Structure| 115467-08-8

Structure of 115467-08-8

Chemical Structure| 115467-08-8

4-Bromo-1-ethoxy-2-fluorobenzene

CAS No.: 115467-08-8

4.5 *For Research Use Only !

Cat. No.: A893765 Purity: 97%

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Product Details of [ 115467-08-8 ]

CAS No. :115467-08-8
Formula : C8H8BrFO
M.W : 219.05
SMILES Code : CCOC1=C(F)C=C(Br)C=C1
MDL No. :MFCD09907659

Safety of [ 115467-08-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 115467-08-8 ]

* 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 [ 115467-08-8 ]

[ 115467-08-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 115467-08-8 ]
  • [ 279263-10-4 ]
YieldReaction ConditionsOperation in experiment
First step 100 ml of a THF solution of 22.8 g (104 mmol) of 3-fluoro-4-ethoxybromobenzene was dropped, while stirring, at 40 to 60C to 3.03 g (124.8 mmol) of dried turnings magnesium, and refluxed under heating after dropping for one hour. The solution was cooled by a coolant to -70C and, a THF solution of 16 ml (132.5 mmol) of trimethyl borate (THF: 70 ml) was dropped under stirring. After stirring at -70C for 3 hours, and further stirring at a room temperature for 20 hours, the reaction solution was cooled to 5C, and 50 ml of 6M hydrochloric acid was added. After separating the organic layer, the aqueous layer was extracted with 100 ml of ethyl acetate. After mixing the organic layer, it was washed with water and then with an aqueous saturated sodium chloride solution successively and, after drying over anhydrous magnesium sulfate, concentrated under a reduced pressure, to obtain 22.3 g of crude 3-fluoro-4-ethoxyphenyl boronic acid.
  • 2
  • [ 121-43-7 ]
  • [ 115467-08-8 ]
  • [ 279263-10-4 ]
YieldReaction ConditionsOperation in experiment
87% Under nitrogen atmosphere,Magnesium (5.76 g) was placed in a reactor, and a solution of compound (T-2) (40.0 g) in tetrahydrofuran (THF) (250 mL) was slowly added to the reactorStir at room temperature for 2 hours. Then a solution of trimethyl borate (28.6 ml, 255.7 mmol) in THF (150 ml) is added,Stir for 12 hours. Then cool to 0 C,1N hydrochloric acid (548 ml) was added and stirred for 2 hours.The reaction mixture was poured into water and the aqueous layer was extracted with ethyl acetate.After washing the combined organic layer with brine,The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure.The residue is purified by recrystallization from heptane,Compound (T-3)(29.3 g; 87%) were obtained.
65% The compound (T-26) (43.8 g) was dissolved in DryTHF (400 ml), and the resultant solution was cooled to -70C. In a nitrogen atmosphere, n-BuLi (133 ml) was added dropwise, and agitation was carried out at -70C for 2 hours. Then, a DryTHF solution of trimethyl borate (64.8 g) was slowly added dropwise at -70C, and the resultant solution was heated to room temperature and agitated for 16 hours. After completion of the reaction, 2N-HCl (200 ml) was added, and then extraction was carried out with toluene, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a light brown solid was obtained. The resultant material was subjected to recrystallization (heptane:toluene = 4:1 in a volume ratio), (T-27) was obtained as a colorless crystal (23.9 g, yield: 65%).
  • 3
  • [ 115467-08-8 ]
  • [ 98121-48-3 ]
YieldReaction ConditionsOperation in experiment
38.0 g Under a nitrogen atmosphere, compound (s21) (80 g, 365 mmol) and metal magnesium (10.65 g, 438 mmol) were added into a reaction vessel, and thus a Grignard reagent was prepared in THF (800 mL). After 2 hours, a THF (110 mL) solution of trimethyl borate (56.0 mL, 474.5 mmol) was added dropwise in the temperature range from -75 C. to -70 C., and the resulting mixture was stirred for 20 hours while returning to 25 C. Thereto, acetic acid (31.3 mL, 547.5 mmol) was added dropwise in the temperature range of 20 C. to 25 C. After 30 minutes, hydrogen peroxide (30% aqueous solution, 82.7 g, 730 mmol) was added dropwise in the temperature range of 25 C. to 35 C., and the resulting mixture was further stirred for 10 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. Combined organic layers were washed with water, an aqueous solution of sodium sulfite, water and saturated brine, and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and then the residue was purified with chromatography on silica gel (heptane:ethyl acetate=20:1 in a volume ratio) and by vacuum distillation (930 Pa), and thus compound (s22) (38.0 g, 243 mmol; 66 mol %) was obtained.
 

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