Reaction #2320138

Reaction equation

K2CO3

4-bromo-4′-hydroxybiphenyl

1-iodopentane

→

4-Bromo-4′-pentyloxybiphenyl

Solvents

2-butanone

Conditions

Workup

1. 1
   Otherconsumption of the bromo alcohol
2. 2
   workup.ADDITIONdiluted with CH2Cl2 (600 ml)
3. 3
   Filtrationfiltered
4. 4
   WashThe filtrate was washed twice with H2O and twice with a saturated aqueous NaCl solution
5. 5
   Dryingdried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Otherdried at reduced pressure
8. 8
   Otherto provide a solid
9. 9
   OtherThis solid was isolated by filtration
10. 10
    Washwashed repeatedly with a total of 2 L of ice-cold heptane
11. 11
    Otherto remove all traces of iodopentane
12. 12
    Otherdried overnight under high vacuum

Procedure

Anhydrous K2CO3 (416 g, 3 mol) was added to a mixture of 4-bromo-4′-hydroxybiphenyl (300 g, 1.2 mol), 1-iodopentane (234 ml, 1.79 mol) and 2-butanone (600 ml). The reaction mixture was refluxed for 44 h until TLC (85:15 hexanes/EtOAc) showed complete consumption of the bromo alcohol. The mixture was cooled to about 30° C., diluted with CH2Cl2 (600 ml) and then filtered. The filtrate was washed twice with H2O and twice with a saturated aqueous NaCl solution, dried over anhydrous Na2SO4, filtered and then dried at reduced pressure to provide a solid. This solid was isolated by filtration, washed repeatedly with a total of 2 L of ice-cold heptane to remove all traces of iodopentane and then dried overnight under high vacuum. Yield: 340 g (88%) of a white powder.

Source