Tetrahydrofuran → HCID 58307094, compound

HRID 1909903Notes

Reaction equation

HRID 1909903 reaction equation
[NH2:1][C:2]1[C:9]([C:10]#[C:11][Si](C)(C)C)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Br:16].O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>O>[NH2:1][C:2]1[C:9]([C:10]#[CH:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Br:16]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11078149TBAF tetrahydrofuranHCID 58306718HCID 58306718, compound

Product 1

HCID 58307094HCID 58307094, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-amino-3-bromo-5-[(trimethylsilyl)ethynyl]benzonitrile (0.80 g) and tetrahydrofuran (3.0 mL) was added a 1 M tetrabutyl ammonium fluoride-THF solution (3.0 mL) under ice-cooling, followed by stirring at room temperature for 0.5 hour. To the reaction mixture was added water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/hexane=30-50%) to obtain 4-amino-3-bromo-5-ethynylbenzonitrile (0.57 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform/hexane=30-50%)

Sources & evidence

ORD record
ord-578f4416a8e74f0da467b2e9d860bc39
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

Loading…