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CAS No. : | 676134-68-2 | MDL No. : | MFCD09744079 |
Formula : | C9H7BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KOROTCDTJPLXMA-UHFFFAOYSA-N |
M.W : | 227.05 | Pubchem ID : | 45489802 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
86% | With methanol; at 20℃; | Step Two; 6-Bromo-isochroman-4-one; 0 Bt . COoH i AD) i . Br C02H 1. Ac2O 0 i OC02H 2. Basic Resin i O A solution of Bromo-2-carboxymethoxymethyl-benzoic acid in acetic anhydride (350 mL) containing potassium acetate (170 g) was heated at reflux for 2 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The phases were separated and the aqueous phase extracted with ethyl acetate. The combined ethyl acetate phase was then washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated to yield a red semi-solid. Purification by flash column chromatography over silica (85 : 15 hexanes/ethyl acetate) gave the enol acetate (7.59 g, 29% for three steps) as a golden syrup : 1H NMR (300 MHz, CDC13) 8 7.37 (dd, J = 8.2, 1.9 Hz, 1H), 7.19 (d, J = 1.9 Hz, 1H), 6.82 (d, J = 8.2 Hz, 1H), 5.04 (s, 2H), 2.29 (s, 3H). Unactivated Dowex 500A OH anion exchange resin (1 g) added in one portion to a solution of the acetate enol acetate (5.95 g, 22.11 mmol) in methanol (50 mL) and the reaction mixture stirred at room temperature overnight. The reaction mixture was gravity filtered and the resin washed with fresh methanol. The combined filtrate was then concentrated under reduced pressure to yield 6-Bromo- isochroman-4-one (4.32 g, 86%) as a yellow oil, which solidified on standing |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium tetrahydroborate; In ethanol; water; at 0 - 20℃; for 2.0h; | Step Three; 6-Bromo-isochroman-4-ol; A solution of sodium borohydride (300 mg, 7.93 mmol) dissolved in a minimum amount of ice cold water was added dropwise at 0 C to a solution of 6-Bromo-isochroman-4-one (1.49 g, 6.56 mmol) in absolute ethanol (27.0 mL). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The phases were separated and the organic phase washed with water and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield 6-Bromo-isochroman-4-ol (1.44 g, 95%) as a white solid |
95% | With sodium tetrahydroborate; In ethanol; at 0 - 20℃; for 2.0h; | A solution of sodium borohydride (300 mg, 7.93 mmol) in a minimum amount of ice cold water was added dropwise at 0 C to a solution of 6- bromo-isochromen-4-one (1.49 g, 6.56 mmol) in absolute ethanol (27.0 mL). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The phases were separated and the organic phase was washed with water and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield 6-Bromo- isochromen-4-ol (1.44 g, 95%) as a white solid :'H NMR (300 MHz, CDCl3) No. 7.40 (dd, J= 8.3, 1.8 Hz, 1H), 7.30 (d, J= 8.3 Hz, 1H), 7.15 (d, J= 1.8 Hz, 1H), 4.63 (ABq, J= 15.3 Hz, 2H), 4.49 (d, J= 8.6 Hz, 1H), 4.07 (dd, J= 12.0, 2.8 Hz, 1 H), 3.83 (dd, J = 12.0, 2.8 Hz, 1 H) 2. 60 (d, J = 9.2 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With Dowex 500A; In methanol; at 20℃; | A solution of bromo-2-carboxymethoxymethyl-benzoic acid in acetic anhydride (350 mL) containing potassium acetate (170 g) was heated at reflux for 2 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The phases were separated and the aqueous phase extracted with ethyl acetate. The combined organic phase was then washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated to yield a red semi-solid. Purification by flash column chromatography over silica (85: 15 hexanes/ethyl acetate) yielded the enol acetate (7.59 g, 29% for three steps) as a golden syrup :'H NMR (300 MHz, Ceci3) 8 7.37 (dd, J= 8.2, 1.9 Hz, 1H), 7.19 (d, J= 1.9 Hz, 1H), 6.82 (d, J= 8.2 Hz, 1H), 5.04 (s, 2H), 2.29 (s, 3H). Unactivated Dowex 500A OH anion exchange resin (1 g) added in one portion to a solution of the acetate enol acetate (5.95 g, 22.11 mmol) in methanol (50 mL) and the reaction mixture stirred at room temperature overnight. The reaction mixture was gravity filtered and the resin washed with fresh methanol. The combined filtrate was then concentrated under reduced pressure to yield 6-bromo-isochromen-4- one (4.32 g, 86%) as a yellow oil, which solidified on standing :'H NMR (300 MHz, Ceci3) 8 7.90 (d, J = 8.3 Hz, 1 H), 7.56 (dd, J = 8.3, 1.7 Hz, 1 H), 7.41 (d, J = 1.7 Hz, 1 H), 4.86 (s, 2H), 4.36 (s, 2H). |
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