Reaction #2329065

Reaction equation

1,3-dichloro-5-methoxybenzene

N-bromosuccinimide

hydrochloric acid

→

subject compound

Yield 67.0%

2-bromo-1,3-dichloro-5-methoxybenzene

Yield 67.0%

Solvents

acetone

Conditions

Workup

1. 1
   ConcentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
2. 2
   Otheran insoluble material was removed by filtration
3. 3
   ConcentrationThe filtrate was concentrated under reduced pressure

Procedure

A solution of 5.0 grams (0.028 mole) of 1,3-dichloro-5-methoxybenzene (commercially available) in 35 mL of acetone was stirred and 5.0 grams (0.028 mole) of N-bromosuccinimide, then one mL of aqueous 10% hydrochloric acid were added. Upon completion of additions the reaction mixture was stirred at ambient temperature during a 30-minute period. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was slurried in 20 mL of hexane and an insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, yielding 4.8 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Source