Bromine → HCID 54448051, compound

HRID 1377857Notes

Reaction equation

HRID 1377857 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([OH:12])[C:5]=1[CH3:13].[Br:15]Br>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5]([CH3:13])=[C:6]([OH:12])[CH:7]=[C:8]([O:10][CH3:11])[C:9]=1[Br:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 53952191HCID 53952191, compound

Product 1

HCID 54448051HCID 54448051, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 23.5 g of 3-hydroxy-5-methoxy-2-methylbenzoic acid methyl ester in 1.3 l of chloroform was added over 1 h at -50° to -60° C. a solution of 19.2 g of bromine in 0.2 l of chloroform. Stirring was continued for 2.5 h at -40° C. and for 2 h at 0° C. The reaction mixture was evaporated in vacuo at 0° C.; the residue was dissolved in a mixture of toluene/ethanol (1:1, v/v) and the solvent was again evaporated in vacuo. This procedure was repeated twice with toluene/ethanol (1:1, v/v), and finally once with toluene. The residue was chromatographed on silica gel using ethyl acetate as eluent and the pure product was crystallized from ethyl acetate to yield 28 g of 2-bromo-3-methoxy-5-hydroxy-6-methylbenzoic acid methyl ester as white crystals, m.p. 105°-110° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo at 0° C.
  2. dissolutionthe residue was dissolved in a mixture of toluene/ethanol (1:1
  3. customv/v) and the solvent was again evaporated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. customthe pure product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ab7e7060bf704a7d9a41161ed9436526
Source dataset
uspto-grants-1997_09
Patent number
US05665746

Reaction notes

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