4-bromo-2-chloro-1-methylbenzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Add NBS (13.171 g, 74 mmol) and benzoyl peroxide (152 mg, 0.63 mmol) to a solution of 4-bromo-2-chlorotoluene (15.2 g, 74 mmol) in carbon tetrachloride (152 mL) and stir for 6 days at 90° C. Cool to 0° C., filter the mixture and concentrate the filtrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (99:1) to obtain the desired intermediate as a yellow oil (12.7 g, 61%). Cool to 0° C. filter the mixture concentrate the filtrate in vacuo Purify by chromatography on silica gel eluting with hexane/EtOAc (99:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Bromo-2-chloro-1-methyl-benzene (2.5 mL, 18.7 mmoles) and N-bromosuccinimide (4.0 g, 22.5 mmoles) were dissolved into 50 mL of CCl4. To this stirring mix was added benzoyl peroxide (0.5 g, 2.1 mmoles) and the solution was irradiated using white light. Enough light intensity was utilized to affect gentle reflux for 2 hours. After this period the mixture was cooled to ambient temperature and benzoyl peroxide (0.5 g, 2.1 mmoles) was added. Again, the mix was irradiated to reflux for a period of 2 hours. After this period the reaction mix was chilled to ambient temperature and was gravity filtered. The filtrate was evaporated in vacuo and the resulting crude residue was purified using flash silica chromatography (0-1% EtOAc/Hexane) to yield 4-bromo-1-bromomethyl-2-chloro-benzene (3.04 g, 60%) as a clear liquid. 1H-NMR (CDCl3): δ 7.57 (d, J=2.0 Hz, 1H), 7.39 (dd, J′=8.3 Hz, J″=1.8 Hz, 1H), 7.31 (d, J=8.1 Hz, 1H), 4.53 (s, 2H). To this stirring mix the solution was irradiated to affect gentle reflux for 2 hours Again, the mix was irradiated to reflux for a period of 2 hours After this period the reaction mix was chilled to ambient temperature filtered The filtrate was evaporated in vacuo the resulting crude residue was purified

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.0 g of 2-chloro-4-bromotoluene are dissolved in 120 ml of CCl4. 4.3 g of NBS and 1.6 g of AIBN are added. The mixture is heated at reflux for 15 hours, water is added, the two phases are separated and then extraction is carried out with CH2Cl2. Purification is carried out by chromatography on a silica column eluted with petroleum ether. 3.8 g of liquid are obtained. The mixture is heated at reflux for 15 hours the two phases are separated extraction Purification eluted with petroleum ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.0 g of 2-chloro-4-bromotoluene are dissolved in 120 ml of CCl4. 4.3 g of NBS and 1.6 g of AIBN are added. The mixture is heated at reflux for 15 hours, water is added, the two phases are separated and then extraction is carried out with CH2Cl2. Purification is carried out by chromatography on a silica column eluted with petroleum ether. 3.8 g of liquid are obtained. The mixture is heated at reflux for 15 hours the two phases are separated extraction Purification eluted with petroleum ether

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir: