Ethanol → Ethyl 3-bromo-2-fluorobenzoate

HRID 522747Notes

Reaction equation

HRID 522747 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH2:17](O)[CH3:18]>CCOC(C)=O>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:17][CH3:18])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27363133-Bromo-2-fluorobenzoic acid

Product 1

HCID 17832538Ethyl 3-bromo-2-fluorobenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-bromo-2-fluorobenzoic acid 1 (25.0 g, 114.15 mmol) in ethanol (400 mL) was added conc. H2SO4 (3 mL) at RT and stirred at reflux temperature for 24 h. The reaction was monitored by LC-MS; after completion of the reaction, the reaction mixture was concentrated to obtain the residue. The residue was diluted with EtOAc (500 mL), washed with water (300 mL), brine (300 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford compound 2 (26.0 g, 92%) as a light yellow liquid. 1H NMR (400 MHz, CDCl3): δ 7.88-7.84 (m, 1H), 7.72-7.69 (m, 1H), 7.08-7.04 (m, 1H), 4.39 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureat reflux temperature for 24 h
  2. customafter completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. customto obtain the residue
  5. washwashed with water (300 mL), brine (300 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-539e6fae1a124264825c4df4093d9d0b
Source dataset
uspto-grants-2016_05
Patent number
US09334261B2

Reaction notes

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