Methanol → Dimethyl 2-bromoterephthalate

HRID 1037049

Reaction equation

HRID 1037049 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:19]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:19])=[O:6])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 186730263-Bromo-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 87741Dimethyl 2-bromoterephthalateYield 98%

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.

Workup

  1. temperatureAfter the addition completion, the reaction mixture was refluxed for 5 h
  2. customThen MeOH was removed
  3. additionwater was added
  4. extractionIt was extracted with EA
  5. washthe organic layer was washed with aqueous sodium bicarbonate solution, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2db9f10a59bb459a9d8a44d6b362e639
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Linked notes

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