반응 #583081

반응 방정식

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

Bromine

→

product

수율 80.0%

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

수율 80.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타A 100 ml three-necked flask, fitted with an efficient reflux condenser
2. 2
   기타drying
3. 3
   workup.ADDITIONtube, and addition funnel
4. 4
   기타(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
   기타) The reaction was then quenched by the slow addition of ice-cold 6M HCl
9. 9
   추출The mixture was extracted with Et2O
10. 10
    세척the combined organic layers washed with water, saturated aqueous NaHCO3, and saturated NaCl
11. 11
    건조before being dried over MgSO4
12. 12
    기타Removal of the solvent
13. 13
    workup.DISTILLATIONunder reduced pressure, and distillation of the residue

실험 절차

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).

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