Methanol → Methyl 3-bromo-4-hydroxybenzoate

HRID 1947282Notes

Reaction equation

HRID 1947282 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].CO>C(Cl)Cl.O>[Br:1][C:13]1[CH:12]=[C:7]([CH:6]=[CH:5][C:4]=1[OH:3])[C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 7456MethylparabenHCID 24408BromineHCID 656671Sodium Pyrosulfite

Product 1

HCID 4778958Methyl 3-bromo-4-hydroxybenzoateYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Dibromine (0.185 L, 3614.92 mmol) was added dropwise a stirred suspension of methyl 4-hydroxybenzoate (500 g, 3286 mmol) in DCM (4 L) at 0° C. under N2. The mixture was left to stir for 24 hrs at RT under N2 (need to trap HBr). A solution of sodium metabisulfite (62.5 g, 329 mmol) in 2 L of water was then added, while keeping the temperature around 15° C., followed by 500 mL of MeOH. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered and concentrated to dryness to afford methyl 3-bromo-4-hydroxybenzoate (710 g, 94%) as a white solid. NMR Spectrum (CDCl3): 3.89 (s, 3H), 5.95 (s, 1H), 7.05 (d, 1H), 7.92 (dd, 1H), 8.19 (d, 1H).

Workup

  1. waitThe mixture was left
  2. customthe temperature around 15° C.
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1634455eb873436b94adf028a6ec9446
Source dataset
uspto-grants-2013_03
Patent number
US08399460B2

Reaction notes

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