1,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene → 1432609-54-5

HRID 928644Notes

Reaction equation

HRID 928644 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[O:10][CH2:11][CH2:12]Cl.C([Li])CCC.CCCCCC>C1COCC1>[Br:9][C:4]1[C:3]2[O:10][CH2:11][CH2:12][C:2]=2[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

4

Reactant 2

HCID 108304061,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 833974101432609-54-5Yield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the compound (2.5 g, 7.4 mmol) obtained in Step 1, THF (50 mL) was added. At −78° C., a 2.6 M n-butyllithium/n-hexane solution (2.9 mL, 7.5 mmol) was added thereto and stirred for 1 hour, and then stirred at room temperature overnight. The solvent was distilled away under reduced pressure. The resulting residue was subjected to reversed-phase HPLC using ODS as a filler, and eluted with a mixture solution of water and acetonitrile, which contained trifluoroacetic acid at 0.1% (v/v). The target fraction was lyophilized to thus obtain the title compound.

Workup

  1. stirringstirred at room temperature overnight
  2. distillationThe solvent was distilled away under reduced pressure
  3. washeluted with a mixture solution of water and acetonitrile, which

Sources & evidence

ORD record
ord-b104654a7d3d4145842a59f52919d19c
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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