反応 #583081

反応方程式

3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone

Bromine

→

product

収率 80.0%

3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone

収率 80.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他A 100 ml three-necked flask, fitted with an efficient reflux condenser
2. 2
   その他drying
3. 3
   workup.ADDITIONtube, and addition funnel
4. 4
   その他(Caution: Exothermic Reaction!) to the mixture at room temperature
5. 5
   workup.STIRRINGthe resulting mixture stirred for 2 hours at room temperature
6. 6
   workup.STIRRING(Note: if stirring stops
7. 7
   workup.STIRRINGuntil stirring resumes
8. 8
   その他) The reaction was then quenched by the slow addition of ice-cold 6M HCl
9. 9
   抽出The mixture was extracted with Et2O
10. 10
    洗浄the combined organic layers washed with water, saturated aqueous NaHCO3, and saturated NaCl
11. 11
    乾燥before being dried over MgSO4
12. 12
    その他Removal of the solvent
13. 13
    workup.DISTILLATIONunder reduced pressure, and distillation of the residue

実験手順

A 100 ml three-necked flask, fitted with an efficient reflux condenser and drying tube, and addition funnel, was charged with a mixture of AlC3 9.5 g (71.4 mmol) and 3 ml of CH2Cl2. The 3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenone (5.0 g, 28.7 mmol), was added dropwise with stirring (Caution: Exothermic Reaction!) to the mixture at room temperature. Bromine, 5.5 g (34.5 mmol), was then added very slowly, and the resulting mixture stirred for 2 hours at room temperature. (Note: if stirring stops, the mixture can be warmed to 70° C. until stirring resumes.) The reaction was then quenched by the slow addition of ice-cold 6M HCl. The mixture was extracted with Et2O and the combined organic layers washed with water, saturated aqueous NaHCO3, and saturated NaCl, before being dried over MgSO4. Removal of the solvent under reduced pressure, and distillation of the residue afforded 5.8 g (80%) of the product as a pale-yellow oil which solidified on standing, bp: 140° C./0.4 mm Hg. 1H NMR (CDCl3): δ 8.11 (1H, d, J=3.0 Hz), 7.61 (1H, dd, J=3.0, 9.0 Hz), 7.31 (1H, d, J=9.0 Hz), 2.72 (2H, t, J=6.0 Hz), 2.01 (2H, t, J=6.0 Hz), 1.28 (6H, s).

出典