N,N-Diethylaniline → HCID 17978192, compound

HRID 1049615Notes

Reaction equation

HRID 1049615 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]#C)[CH:3]=1.[F-].[Cs+].[CH2:14](N(CC)C1C=CC=CC=1)C>C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[CH:14]=[C:9]([CH3:10])[O:8][C:4]=2[CH:5]=[CH:6][CH:7]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:14]=[C:9]([CH3:10])[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 7061N,N-DiethylanilineHCID 25953Cesium fluorideHCID 138392491-Bromo-3-(prop-2-yn-1-yloxy)benzene(WXC08380)

Product 2

HCID 17978192HCID 17978192, compoundYield 87%HCID 21251469HCID 21251469, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
190 °C

Procedure

To a solution of 49 (21 mmol) in N, N-diethylaniline (30 mL), cesium fluoride (11 mmol) was added and the mixture was heated at 190° C. for 24 h. After cooling, the suspension was diluted with ethyl acetate (100 mL) and washed with dil HCl (3×50 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated by rotary evaporation and purified column chromatography to give 4-bromo-2-methylbenzofuran (46g, 87%) and 6-bromo-2-methylbenzofuran (13%). The resulting mixture was purified by reverse phase HPLC using 10:1 acetonitrile: water with 0.1% TFA (B) for 22 min followed by 3 min at 100% B, to give compound 46g (26%).

Workup

  1. temperatureAfter cooling
  2. washwashed with dil HCl (3×50 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. custompurified column chromatography

Sources & evidence

ORD record
ord-ce6c23306bdc4028b9d13f089be59e79
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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