Water → Methyl 5-bromo-4-ethyl-2-hydroxybenzoate

HRID 629471Notes

Reaction equation

HRID 629471 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([OH:13])[CH:4]=1)[CH3:2].[Br:14]Br.O>C(O)(=O)C>[Br:14][C:12]1[C:3]([CH2:1][CH3:2])=[CH:4][C:5]([OH:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 54092218Methyl 4-ethyl-2-hydroxybenzoate

Product 1

HCID 118468133Methyl 5-bromo-4-ethyl-2-hydroxybenzoateYield 107.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 4-ethyl-2-hydroxybenzoate (1.43 g) in acetic acid (15.0 mL) was added bromine (1.40 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hr under argon atmosphere. To the reaction mixture was added water, the resulting solid was collected by filtration, and dried under reduced pressure to give the title compound (2.21 g) as a mixture with methyl 3,5-dibromo-4-ethyl-2-hydroxybenzoate (2:1). This compound was used in the next step without an additional purification.

Workup

  1. temperaturecooling
  2. filtrationthe resulting solid was collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-e74eab0a62dc4172aace3357622e9356
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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