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

HRID 629350Notes

Reaction equation

HRID 629350 reaction equation
[CH:1]1([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:14])[CH:5]=2)[CH2:3][CH2:2]1.[Br:15]Br.O>C(O)(=O)C>[Br:15][C:13]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:5][C:6]([OH:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 90423168Methyl 4-cyclopropyl-2-hydroxybenzoate

Product 1

HCID 90423584Methyl 5-bromo-4-cyclopropyl-2-hydroxybenzoateYield 89.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 4-cyclopropyl-2-hydroxybenzoate (1.80 g) in acetic acid (15.0 mL) was added dropwise bromine (1.57 g) under ice-cooling. The mixture was stirred at room temperature for 2 hr, to the reaction mixture was added water, and the resulting solid was collected by filtration. The obtained solid was dried under reduced pressure to give the title compound (2.28 g).

Workup

  1. temperaturecooling
  2. filtrationthe resulting solid was collected by filtration
  3. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-07a03c3e265c4c3bbd5df6829b845b02
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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