تفاعل #1333836

معادلة التفاعل

1-bromo-3-fluoro-5-benzyloxybenzene

1-Bromo-3-fluoro-5-benzyloxybenzene

N,N-dimethylaniline

aluminium chloride

→

sub-title compound

المردود 92.6%

3-Bromo-5-fluorophenol

المردود 92.6%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىthe ice bath was removed
2. 2
   workup.WAITthe stirring was continued for 2 h
3. 3
   أخرىThe reaction was quenched by the cautious addition of 3N HCl (600 mL)
4. 4
   أخرىThe layers were separated
5. 5
   استخلاصthe aqueous layer was extracted with CH2Cl2 (2×150 mL)
6. 6
   غسيلThe combined organic extracts were washed with 2N HCl (250 mL) and H2O (3×250 mL)
7. 7
   workup.ADDITIONTo the organic layer was added 15% KOH (500 mL)
8. 8
   أخرىthe layers were separated
9. 9
   استخلاصThe organic layer was further extracted with 2 N KOH (2×70 mL)
10. 10
    غسيلThe combined aqueous layers were washed with CH2Cl2 (3×100 mL)
11. 11
    استخلاصThe aqueous layer was extracted with Et2O (3×125 mL)
12. 12
    تجفيفthe combined Et2O extracts were dried (Na2SO4)
13. 13
    ترشيحfiltered
14. 14
    تركيزconcentrated in vacuo

الإجراء التجريبي

To a solution of 1-bromo-3-fluoro-5-benzyloxybenzene (110.0 g, 0.39 mol; see step (i) above) and N,N-dimethylaniline (474.0 g, 3.92 mol) in anhydrous CH2Cl2 (1.0 L) at 0° C. was added aluminium chloride (156.0 g, 1.17 mol). After 10 min, the ice bath was removed and the stirring was continued for 2 h. The reaction was quenched by the cautious addition of 3N HCl (600 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×150 mL). The combined organic extracts were washed with 2N HCl (250 mL) and H2O (3×250 mL). To the organic layer was added 15% KOH (500 mL), and the layers were separated. The organic layer was further extracted with 2 N KOH (2×70 mL). The combined aqueous layers were washed with CH2Cl2 (3×100 mL) and then acidified with 4N HCl. The aqueous layer was extracted with Et2O (3×125 mL) then, the combined Et2O extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the sub-title compound (69.0 g, 92%) as a brown oil that was used without further purification.

المصدر