Ethanol → Ethyl 3-Bromo-5-fluorobenzoate

HRID 269555Notes

Reaction equation

HRID 269555 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([F:16])[CH:15]=1)[C:10]([OH:12])=[O:11].[CH2:17](O)[CH3:18]>C(OCC)C.O>[Br:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([F:16])[CH:15]=1)[C:10]([O:12][CH2:17][CH3:18])=[O:11]

Participants

6

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27733393-Bromo-5-fluorobenzoic acid

Product 1

HCID 43476807Ethyl 3-Bromo-5-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sulphuric acid (0.5 mL) was added to a stirring solution of 3-bromo-5-fluorobenzoic acid (473 mgs, 2.16 mmol) in ethanol (10 mL) and refluxed for 17 hours. The reaction mixture was cooled to room temperature and diluted with diethyl ether and water. The ether layer was washed with 5% sodium hydrogen carbonate solution, dried over magnesium sulphate and evaporated to dryness to give the title compound as a brown oil. (506 mg).

Workup

  1. temperaturerefluxed for 17 hours
  2. washThe ether layer was washed with 5% sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b5ddce8d41944fb2a45960cd69bface4
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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