反应详情

A mixture of bromobenzene (0.3 mol) in THF (300 ml) was added dropwise to a mixture of magnesium (0.32 mol) in THF (20 ml). The mixture was stirred and refluxed for 1 hour. A mixture of 4-biphenylcarboxaldehyde (0.3 mol) in THF (500 ml) was added dropwise. The mixture was stirred and refluxed for 2 hours, at room temperature overnight, poured out into a saturated NH4Cl solution and extracted with DCM. The organic layer was separated, washed three times, dried, filtered and the solvent was evaporated. The residue was triturated in hexane, filtered off and purified over silica gel on a glass filter (eluent: CH2Cl2 100%). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE, filtered off and dried, yielding 31 g of (±)-α-phenyl(1,1′-biphenyl)-4-methanol (interm. 23).

1. temperaturerefluxed for 1 hour
2. additionwas added dropwise
3. stirringThe mixture was stirred
4. extractionextracted with DCM
5. customThe organic layer was separated
6. washwashed three times
7. customdried
8. filtrationfiltered
9. customthe solvent was evaporated
10. customThe residue was triturated in hexane
11. filtrationfiltered off
12. custompurified over silica gel on a glass
13. filtrationfilter (eluent: CH2Cl2 100%)
14. customThe pure fractions were collected
15. customthe solvent was evaporated
16. customThe residue was triturated in DIPE
17. filtrationfiltered off
18. customdried