Reaction #1124231

Reaction equation

3-bromo-4-(methoxycarbonyl)benzoic acid

SOCl2

MeOH

→

dimethyl 2-bromoterephthalate

Yield 98.0%

Conditions

Workup

1. 1
   TemperatureAfter the addition completion, the reaction mixture was refluxed for 5 h
2. 2
   OtherThen MeOH was removed
3. 3
   workup.ADDITIONwater was added
4. 4
   ExtractionIt was extracted with EA
5. 5
   Washthe organic layer was washed with aqueous sodium bicarbonate solution, brine
6. 6
   Dryingdried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure

Procedure

To a solution of 3-bromo-4-(methoxycarbonyl)benzoic acid (3.0 g, 11.6 mmol) in MeOH (50 mL) was slowly added SOCl2 (2.76 g, 23.2 mmol) dropwise. After the addition completion, the reaction mixture was refluxed for 5 h. Then MeOH was removed and water was added. It was extracted with EA and the organic layer was washed with aqueous sodium bicarbonate solution, brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give dimethyl 2-bromoterephthalate (3.1 g, yield 98%) as a white solid. It was used without further purification in the next step.

Source