Reaction #833518

Reaction equation

DMF

NBS

1b

1,2-di(2-ethylhexyloxy)benzene

NBS

→

4-bromo-1,2-di(2-ethylhexyloxy)benzene

Yield 96.0%

Solvents

water

Conditions

Workup

1. 1
   WashThe organic layer was washed with a saturated LiCl solution and water
2. 2
   DryingAfter drying with MgSO4 the solvent
3. 3
   Otherwas removed under reduced pressure
4. 4
   workup.DISTILLATIONThe remaining oil was distilled (160° C./0.01 mmHg)

Procedure

Solid NBS (26.21 g, 0.147 mol) was added to an ice cold CH2Cl2 solution (250 mL) of 1b under N2 in the absence of light. Just enough DMF was added (30 mL) to dissolve the NBS. The reaction mixture was allowed to warm to room temperature and then stirred for 12 h. The mixture was then poured into water. The organic layer was washed with a saturated LiCl solution and water. After drying with MgSO4 the solvent was removed under reduced pressure. The remaining oil was distilled (160° C./0.01 mmHg) to yield 4-bromo-1,2-di(2-ethylhexyloxy)benzene (2b) in 96% yield as a colorless oil.

Source