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CAS No. : | 400822-47-1 | MDL No. : | MFCD08063822 |
Formula : | C9H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | USONNBCBJMNJIU-UHFFFAOYSA-N |
M.W : | 213.07 | Pubchem ID : | 22259686 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
47% | Step 1: A solution of <strong>[100189-84-2]2,5-dibromoxylene</strong> (2.0 g, 7.6 mmol) in DCM (20 ml) was treated with n-BuLi (2.5 M solution in hexane, 3 ml, 1.0 equiv.) at -78C. After stirring for 1h, DMF (1.8 ml, 23 mmol, 3 eq.) was added and the solution was allowed to warm to room temperature. It was acidified to pH 2 with 5% hydrochloric acid and extracted with diethyl ether (3x50 ml). The combined organic phase was dried and evaporated and the residue was purified by column chromatography using PE:EA = 10:1 as eluent to give 4-bromo-3,5-dimethylbenzaldehyde (0.76 g, yield: 47%). | |
A solution of <strong>[100189-84-2]2,5-dibromoxylene</strong> (8.0 g, 30.3 mmol) in diethyl ether (120 mL) is cooled to -78 C. and then treated with n-buthyllithium (20 mL, 1.6 M in hexane). After stirring for 40 min, DMF (6 mL) is slowly added. The mixture is warmed to rt and stirred for 1 h. The mixture is cooled again to -78 C. before another portion of n-butyllithium (5 mL) is added. The reaction mixture is allowed to warm to rt and stirred for another hour. The reaction is quenched by adding 5% aq. HCl. The mixture is extracted with EA, and the extract is concentrated in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 4-bromo-3,5-dimethyl-benzaldehyde (8.2 g) as a white soft solid. | ||
A solution of <strong>[100189-84-2]2,5-dibromoxylene</strong> (8.0 g, 30.3 mmol) in diethyl ether (120 ml_) is cooled to -78C and then treated with n-buthyllithium (20 ml_, 1.6 M in hexane). After stirring for 40 min, DMF (6 ml_) is slowly added. The mixture is warmed to rt and stirred for 1 h. The mixture is cooled again to -78C before another portion of n- butyllithium (5 ml_) is added. The reaction mixture is allowed to warm to rt and stirred for another hour. The reaction is quenched by adding 5% aq. HCI. The mixture is extracted with EA, and the extract is concentrated in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 4-bromo- 3,5-dimethyl-benzaldehyde (8.2 g) as a white soft solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; n-butyllithium; In diethyl ether; hexane; N,N-dimethyl-formamide; | a) A solution of <strong>[100189-84-2]2,5-dibromoxylene</strong> (8.0 g, 30.3 mmol) in diethyl ether (120 mL) is cooled to -78C and then treated with n-buthyllithium (20 mL, 1.6 M in hexane). After stirring for 40 min, DMF (6 mL) is slowly added. The mixture is warmed to rt and stirred for 1 h. The mixture is cooled again to -78C before another portion of n-butyllithium (5 mL) is added. The reaction mixture is allowed to warm to rt and stirred for another hour. The reaction is quenched by adding 5% aq. HCl. The mixture is extracted with EA, and the extract is concentrated in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 4-bromo-3,5-dimethyl-benzaldehyde (8.2 g) as a white soft solid. |