Methylparaben → Methyl 3-bromo-4-hydroxybenzoate

HRID 385068Notes

Reaction equation

HRID 385068 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12]Br>C(Cl)(Cl)Cl.CO>[Br:12][C:11]1[CH:10]=[C:5]([CH:4]=[CH:3][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 7456MethylparabenHCID 24408Bromine

Product 1

HCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent3×

Procedure

Methyl 4-hydroxybenzoate (25.00 g) was dissolved in chloroform (225 mL) and methanol (25 mL), and a chloroform (30 mL) solution of bromine (8.5 mL) was added dropwise to the solution, and then the mixture was stirred for 2 hours. The reaction solution was diluted with chloroform, washed with water, an aqueous 10% sodium thiosulfate solution and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (37.81 g) as a colorless crystal.

Workup

  1. washwashed with water
  2. dry with materialan aqueous 10% sodium thiosulfate solution and saturated brine and then dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e4955609e5b54c14a820fbc8ae109713
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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