تفاعل #2700

معادلة التفاعل

4-bromotoluene

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

Compound A

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

→

title compound

1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

المذيبات

THF

THF

THF

ethylacetate

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated to 70° C. for 30 minutes
2. 2
   درجة الحرارةAfter cooling to ambient temperature
3. 3
   درجة الحرارةheated to 70° C. for 24 hours
4. 4
   درجة الحرارةThe mixture was cooled to ambient temperature
5. 5
   أخرىthe reaction was quenched by addition of H2O
6. 6
   workup.ADDITIONThe mixture was diluted with ether:ethylacetate (1:1, 100 mL)
7. 7
   غسيلwashed with saturated NH4Cl (15 mL), water (10 mL) and brine (10 mL)
8. 8
   تجفيفThe organic layer was dried with MgSO4
9. 9
   أخرىSolvent was removed under reduced pressure
10. 10
    أخرىto afford the crude product as an off
11. 11
    درجة الحرارةthe mixture was refluxed for 16 hours
12. 12
    درجة الحرارةThe mixture was cooled to ambient temperature
13. 13
    غسيلwashed with 10% NaHCO3 (20 mL), brine (20 mL)
14. 14
    تجفيفdried with MgSO4
15. 15
    أخرىthe solvent wasremoved by evaporation
16. 16
    أخرىPurification by chromatography on silica gel

الإجراء التجريبي

To a mixture of Mg metal (650 mg, 27 mmol) in THF (20 mL) was added 4-bromotoluene (5.3 g, 31 mmol) in THF (40 mL). The mixture was stirred for 2 hours at ambient temperature and heated to 70° C. for 30 minutes. After cooling to ambient temperature, 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A) (2.1 g, 8 mmol), in THF (5 mL) was added and heated to 70° C. for 24 hours. The mixture was cooled to ambient temperature and the reaction was quenched by addition of H2O. The mixture was diluted with ether:ethylacetate (1:1, 100 mL) and washed with saturated NH4Cl (15 mL), water (10 mL) and brine (10 mL). The organic layer was dried with MgSO4. Solvent was removed under reduced pressure to afford the crude product as an off. The product was dissolved in THF (20 mL). To this solution p-toleune sulfonic acid (pTSA) (35 mg) was added and the mixture was refluxed for 16 hours. The mixture was cooled to ambient temperature, diluted with ethylacetate (160 mL), washed with 10% NaHCO3 (20 mL), brine (20 mL), dried with MgSO4 and the solvent wasremoved by evaporation. Purification by chromatography on silica gel gave the title compound as a white solid.

المصدر