HCID 59508382, compound → HCID 83410482, compound

HRID 923683Notes

Reaction equation

HRID 923683 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10](OCC)OCC)=[CH:4][C:3]=1[F:17]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH:9]=[CH:10][C:4]=2[C:3]=1[F:17]

Participants

3

Reactant 1

HCID 59508382HCID 59508382, compound

Product 1

HCID 83410482HCID 83410482, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Bromo-4-(2,2-diethoxyethoxy)-2-fluorobenzene (11.4 g, 0.037 mol) was dissolved in toluene (78 mL). Polyphosphoric acid (11.9 g) was added and the mixture was heated to reflux for 5 h. The solvent was removed and the residue was diluted with water and ethyl acetate. The organic phase was washed with 2M NaOH solution and then dried over Na2SO4. A mixture of 5-bromo-6-fluorobenzofuran and 5-bromo-4-fluorobenzofuran (4.8 g, 60.3%) were obtained as a mixture after purification via column chromatography.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 h
  3. customThe solvent was removed
  4. additionthe residue was diluted with water and ethyl acetate
  5. washThe organic phase was washed with 2M NaOH solution
  6. dry with materialdried over Na2SO4
  7. additionA mixture of 5-bromo-6-fluorobenzofuran

Sources & evidence

ORD record
ord-82a6d891555d45d0b804867d57c1c421
Source dataset
uspto-grants-2016_03
Patent number
US09278985B2

Reaction notes

Loading…