Ethanol → Ethyl 3-bromo-5-methylbenzoate

HRID 1767242Notes

Reaction equation

HRID 1767242 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:12](O)[CH3:13]>S(=O)(=O)(O)O.C(OCC)C.O>[CH2:12]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:2]([Br:1])[CH:3]=1)[CH3:13]

Participants

5

Reactant 2

HCID 702EthanolHCID 34331273-Bromo-5-methylbenzoic acid

Product 1

HCID 20086624Ethyl 3-bromo-5-methylbenzoateYield 94%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 21584184Diethylether waterSolvent

Conditions

Temperature
90 °C

Procedure

Sulphuric acid (10 drops) was added to 3-bromo-5-methylbenzoic acid (1.18 g, 5.49 mmol) in ethanol (20 ml) and refluxed at 90° C. for 20 hours. After cooling, the mixture was diluted with diethyl ether/water and the organic phase washed with sodium hydrogen bicarbonate (saturated solution), dried (magnesium sulphate) and evaporated to dryness to give the title compound as a pale yellow oil (1.249 g, 94%).

Workup

  1. temperatureAfter cooling
  2. washthe organic phase washed with sodium hydrogen bicarbonate (saturated solution)
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-f743fbd499fe4d2e9d01a567776bde30
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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