Methyl Salicylate → Methyl 5-bromosalicylate

HRID 484778Notes

Reaction equation

HRID 484778 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][C:7]1[CH:8]=[C:2]([C:1]([O:10][CH3:11])=[O:9])[C:3]([OH:4])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4133Methyl SalicylateHCID 24408Bromine

Product 1

HCID 77683Methyl 5-bromosalicylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 152 g (1.0 mole) of methyl salicylate and 500 ml of chloroform were added dropwise with stirring a solution of 172 g (1.08 mole) of bromine in 300 ml of chloroform at about 10° C. over a period of 6 hours. After the addition, the mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed with water and then with an aqueous solution of sodium bicarbonate. Removal of the solvent gave 230 g of substantially pure methyl 5-bromosalicylate in 99.6% yield, M.P. 59° to 61.5° C.

Workup

  1. additionwere added dropwise
  2. additionAfter the addition
  3. washThe reaction mixture was washed with water
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-d08f0f85919b49ba9f67d6af6fda3bb8
Source dataset
uspto-grants-1985_08
Patent number
US04533732

Reaction notes

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