Bromine → Methyl 5-bromo-2-hydroxy-4-methoxybenzoate

HRID 34962

Reaction equation

HRID 34962 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([OH:15])[C:8](=[CH:13][CH:14]=1)[C:9]([O:11][CH3:12])=[O:10]>C(Cl)Cl>[Br:1][C:14]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:15])=[CH:6][C:5]=1[O:4][CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 1051517Methyl 5-bromo-2-hydroxy-4-methoxybenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.0 g (56.5 mmol) of bromine in 5 ml of CH2Cl2 is added dropwise to a 0° C. solution of 10.0 g (54.9 mmol) of methyl 4-methoxysalicylate in 90 ml of CH2Cl2. The reaction is stirred at 0° C. to 25° C. over five hours and then concentrated in vacuo to give 13.9 g of methyl 5-bromo-4-methoxysalicylate as a white solid: mp 141°-143° C.) (lit mp 143°-144° C.), Cresp, T. M.; Sargent, M. V.; Elix, J. A.; Murphy, D. P. H., J. Chem. Soc., Perkin Trans., 1, 1973, 340). The material is sufficiently pure to be used in the subsequent reaction.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c83c3657298944b6a8269e1c4ff4b7c4
Source dataset
uspto-grants-1988_08
Patent number
US04764525

Linked notes

Loading…