Boron trifluoride etherate → HCID 57445080, compound

HRID 2277638Notes

Reaction equation

HRID 2277638 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][CH2:12][Mg+].[Br-].B(F)(F)F.CCOCC>CCOCC>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]1([NH2:5])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 1189392-Bromo-4-fluorobenzonitrileHCID 178461630HCID 178461630, compound

Product 1

HCID 57445080HCID 57445080, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) and Ti(Oi-Pr)4 (9.05 mL, 27.5 mmol) in ether (100 mL) at −78° C. was added EtMgBr (18.3 mL, 55 mmol) dropwise. The solution was allowed to warm to room temperature and stirred for 1 hour before BF3-Et2O (6.25 mL) was added and stirring continued at room temperature for another 1 hour. The reaction solution was quenched with 1 N HCl solution, and washed with EtOAc. The aqueous layer was adjusted to pH˜10 with aq. NaOH (2 N) solution and then exacted with EtOAc (3×). The combined organic layers were dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The residue was then purified by column chromatography to give title compound (3.0 g, yield 52.2%) as yellowish oil.

Workup

  1. additionwas added
  2. customThe reaction solution was quenched with 1 N HCl solution
  3. washwashed with EtOAc
  4. customThe combined organic layers were dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-02a09a2719ed43afa8a980fbaa20981a
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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