Acetic Acid → Ethyl 3-bromo-6-hydroxy-2-methylbenzoate

HRID 365954

Reaction equation

HRID 365954 reaction equation
[Br:1]Br.C(O)(=O)C.[CH3:7][C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([OH:19])[CH:11]=[CH:10][CH:9]=1>O.C(OCC)(=O)C>[Br:1][C:9]1[CH:10]=[CH:11][C:12]([OH:19])=[C:13]([C:8]=1[CH3:7])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 24408BromineHCID 584222Ethyl 2-hydroxy-6-methylbenzoate

Product 1

HCID 23293235Ethyl 3-bromo-6-hydroxy-2-methylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of bromine (5.05 ml, 0.099 mol) and acetic acid (15 ml) is added to a mixture of ethyl 6-methyl-2-hydroxybenzoate (17.05 g, 0.095 mol), and acetic acid (15 ml) at a temperature of 20° C. The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with water and ethyl acetate. The organic phase is washed with water twice, concentrated in vacuo and the residue is purified by flash chromatography (petrol ethers:ethyl acetate, 98:2 v/v) yielding the pure product as a yellow oil, 21.7 g, (88.2%).

Workup

  1. washThe organic phase is washed with water twice
  2. concentrationconcentrated in vacuo
  3. customthe residue is purified by flash chromatography (petrol ethers:ethyl acetate, 98:2 v/v)

Sources & evidence

ORD record
ord-a7b02d0bff1d45a7a3200b6dadfc077f
Source dataset
uspto-grants-2000_10
Patent number
US06127570

Linked notes

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