Boron trifluoride → HCID 67294860, compound

HRID 589203Notes

Reaction equation

HRID 589203 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[CH2:11]([Mg]Br)[CH3:12].B(F)(F)F>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2([NH2:7])[CH2:12][CH2:11]2)=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 3

HCID 6356Boron trifluorideHCID 7360294-Bromo-2-fluorobenzonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 67294860HCID 67294860, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 4-bromo-2-fluorobenzonitrile (432 mg, 2.16 mmol) in THF (10 mL) at −78° C., was added titanium (IV) isopropoxide (0.7 mL, 2.4 mmol). After stirring for 10 minutes, ethylmagnesium bromide (1M, 4.75 mL, 4.75 mmol) was added and the reaction mixture warmed to 0° C. and then to rt. BF3.OEt (0.53 mL, 4.32 mmol) was then added and the reaction mixture stirred for an additional 1 h at rt. The reaction was quenched with saturated NH4Cl and NaOH (1N). Extraction with EtOAc, and drying over MgSO4 yielded crude product which was taken forward as crude in the next step. HPLC-MS tR=0.34 min (UV254 nm); mass calculated for formula C9H9BrFN 228.99, observed LCMS m/z 230.0 (M+H).

Workup

  1. customto rt
  2. additionOEt (0.53 mL, 4.32 mmol) was then added
  3. stirringthe reaction mixture stirred for an additional 1 h at rt
  4. customThe reaction was quenched with saturated NH4Cl and NaOH (1N)
  5. extractionExtraction with EtOAc
  6. dry with materialdrying over MgSO4
  7. customyielded crude product which

Sources & evidence

ORD record
ord-9e1672073c2247d8864546e807614a11
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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