Alternatived Products of [ 1132672-05-9 ]
Product Details of [ 1132672-05-9 ]
| CAS No. : | 1132672-05-9 |
MDL No. : | MFCD14584686 |
| Formula : |
C10H13BrO3
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
261.11
|
Pubchem ID : | - |
| Synonyms : |
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Safety of [ 1132672-05-9 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 1132672-05-9 ]
* 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 [ 1132672-05-9 ]
- 1
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[ 37942-01-1 ]
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[ 6482-24-2 ]
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[ 1132672-05-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 74% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h; |
1 Synthesis of Intermediate 1b:
Compound 1a (40.4g, 200.0mmol), 1-bromo-2-methoxyethane (27.6g, 200.0mmol) and potassium carbonate (33.1g, 240.0mmol) were dissolved in DMF (500mL) and the temperature was raised to 60 °C stir and react at for 6 hours, TLC detects the reaction. After the reaction is completed, add water (500mL) to quench the reaction. It was extracted with ethyl acetate (500mL 2), the organic layer was dried, filtered, concentrated, and separated by column chromatography to obtain 38.5 g of off-white solid with a yield of 74.0%. |
| 45 g |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h; |
134.1 Preparation of 4-bromo-1-methoxy-2-(2-methoxyethoxyl)benzene
To a solution of 5-bromo-2-methoxylphenol (50 g, 0.25 mol, Accela) in DMF (200 ml) was added potassium carbonate (70 g, 0.5 mol) and 1-bromo-2-methoxy-ethane (42 g, 0.3 mol, Sinopharm Chemical). The resulting mixture was heated at 90° C. for 8 h. After being cooled to room temperature, the mixture was poured into water (500 mL) and the aqueous solution was extracted with ethyl acetate (400 mL*2). The organic layers were combined and washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give 4-bromo-1-methoxy-2-(2-methoxyethoxyl)benzene (45 g) as a white solid, which was used directly in the next step without further purification. |
| 45 g |
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 8h; |
134.1 Step 1: Preparation of 4-bromo- 1 -methoxy-2-(2-methoxyethoxy)benzene
Step 1: Preparation of 4-bromo- 1 -methoxy-2-(2-methoxyethoxy)benzene To a solution of 5 - b ro mo - 2 - m c t ho x y 1 p h e no 1 (50 g, 0.25 mol, Accela) in DMF (200 ml) was added potassium carbonate ( 70 g, 0.5 mol) and 1 - b ro mo - 2 - me t ho x y- et h a n e (42 g, 0.3 mol, Sinopharm Chemical). The resulting mixture was heated at 90 °C for 8 h. After being cooled to room temperature, the mixture was poured into water (500 ml. ) and the aqueous solut ion was extracted with ethyl acetate (400 ΠΙΙ 2 ). The organic layers were combined and washed with water and brine, dried over anhydrous Na2S04, and concentrated under reduced pressure to give 4-bromo- l -methoxy-2-(2-methoxycthoxy)benzcne (45 g) as a white solid, which was used directly in the next step without further purification. |
| 0.65 g |
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; |
58.1 Step 1: Preparation of 4-bromo-1-methoxy-2-(2-methoxyethoxy)benzene
A mixture of 5-bromo-2-methoxy-phenol (0.50 g, 2.46 mmol), 1-bromo-3-methoxy- propane (1.03 g, 7.39 mmol) and potassium carbonate (1.02 g, 7.39 mmoi) in DMF (5 mL) washeated with stirring at 120 °C for 4 hrs. The resulting reaction mixture was cooled to rt, diluted with water (15 rnL) and extracted with EA (20 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 4- bromo-1-methoxy-2-(2-methoxyethoxy)benzene (0.65 g), which was used in the next step without further purification. |
- 2
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[ 1132672-05-9 ]
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[ 1567-75-5 ]
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2-[4-methoxy-3-(2-methoxyethoxyl)phenyl]-1-(1-methylcyclopropyl)ethanone
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 25 g |
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In tetrahydrofuran at 60℃; for 8h; Inert atmosphere; |
134.2 Preparation of 2-[4-methoxy-3-(2-methoxyethoxyl)phenyl]-1-(1-methylcyclopropyl)ethanone
Step 2: To a solution of 4-bromo-1-methoxy-2-(2-methoxyethoxyl)benzene (21.4 g, 82 mmol) in THF (300 mL) was added 1-(1-methylcyclopropyl)ethanone (16 g, 164 mmol, TCI), Pd2(dba)3 (1.13 g, 1.23 mmol), Xantphos (1.42 g, 2.46 mmol) and sodium tert-butoxide (26.0 g, 270 mmol). The resulting mixture was stirred for 8 h at 60° C. under argon atmosphere. After being cooled to room temperature, the resulting suspension was filtered with suction, the filter cake was poured into water and acidified to pH=3 with 2 M hydrochloride acid. The mixture was extracted with ethyl acetate (400 mL*2) and the combined organic layers were washed with water (200 mL) and brine, dried over anhydrous Na2SO4 and concentrated to give 2-[4-methoxy-3-(2-methoxyethoxyl)phenyl]-1-(1-methylcyclopropyl)ethanone (25 g) as a yellow oil. |
| 25 g |
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In tetrahydrofuran at 60℃; for 8h; Inert atmosphere; |
134.2 Step 2: Preparation of 2-|4-methoxy-3-(2-methoxyethoxy)phenyl|-l-( l - meth lcvcloprop l)ethanone
Step 2: Preparation of 2-|4-methoxy-3-(2-methoxyethoxy)phenyl|-l-( l - meth lcvcloprop l)ethanone To a solution of 4-bromo-l-methoxy-2-(2-methoxyethoxy)benzene (2 1 .4 g. 82 mmol) in THF (300 ml. ) was added 1 -( 1 -methylcyclopropyl )ethanone (16 g, 164 mmol, TCI), Pd2(dba)3 ( 1 . 1 3 g, 1 .23 mmol), Xantphos ( 1 .42 g, 2.46 mmol ) and sodium fert-butoxide (26.0 g, 270 mmol ). The result ing mixture was st irred for 8 h at 60 °C under argon atmosphere. After being cooled to room temperature, the resulting suspension was filtered with suction, the filter cake was poured into water and acidified to pH=3 with 2 M hydrochloride acid. The mixture was extracted with ethyl acetate (400 ml 2 ) and the combined organic layers were washed with water ( 200 ml. ) and brine, dried over anhydrous Na^SO^ and concentrated to give 2-[4-methoxy-3-(2- methoxyethoxy)phenyl]- 1 -( 1 -methylcyclopropyl )cthanonc (25 g) as a yellow oil. |
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