تفاعل #705200

معادلة التفاعل

AlCl3

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

Bromine

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product

المردود 80.0%

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

المردود 80.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىA 100 ml three-necked flask, fitted with an efficient reflux condenser
2. 2
   أخرىdrying
3. 3
   workup.ADDITIONtube, and addition funnel
4. 4
   workup.STIRRINGthe resulting mixture stirred for 2 hours at room temperature
5. 5
   workup.STIRRING(Note: if stirring stops
6. 6
   درجة الحرارةthe mixture can be warmed to 70° C.
7. 7
   workup.STIRRINGuntil stirring resumes
8. 8
   أخرى) The reaction was then quenched by the slow addition of ice-cold 6M HCl
9. 9
   استخلاصThe mixture was extracted with Et2O
10. 10
    غسيلthe combined organic layers washed with water, saturated aqueous NaHCO3, and saturated NaCl
11. 11
    تجفيفbefore being dried over MgSO4
12. 12
    أخرىRemoval of the solvent
13. 13
    workup.DISTILLATIONunder reduced pressure, and distillation of the residue

الإجراء التجريبي

A 100 ml three-necked flask, fitted with an efficient reflux condenser and drying tube, and addition funnel, was charged with a mixture of AlCl3 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).

المصدر