3-Bromo-2-fluorobenzonitrile → 3-Bromo-2-tert-butoxy-benzonitrile

HRID 2403979Notes

Reaction equation

HRID 2403979 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:11][C:12]([CH3:15])([O-:14])[CH3:13].[K+]>O1CCCC1>[Br:1][C:2]1[C:3]([O:14][C:12]([CH3:15])([CH3:13])[CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 27612003-Bromo-2-fluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 582706613-Bromo-2-tert-butoxy-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-bromo-2-fluoro-benzonitrile (40.0 g, 0.200 mol) and tetrahydrofuran (200 mL) was chilled to 0° C. and stirred for 5 min. A solution of potassium tert-butoxide (130 mL, 0.210 mol) was added dropwise at 0° C. and the reaction was allowed to warm to RT with stirring over 90 min. The reaction was quenched with water (200 mL) and 2 M Na2CO3 (100 mL) and extracted with EtOAc (3×200 mL). The organic layer was dried over Na2SO4 and the solvent was removed by rotary evaporation to provide the title compound as a light yellow oil.

Workup

  1. temperatureto warm to RT
  2. stirringwith stirring over 90 min
  3. customThe reaction was quenched with water (200 mL) and 2 M Na2CO3 (100 mL)
  4. extractionextracted with EtOAc (3×200 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-68ec76ab6011434ab16b6b18375a5864
Source dataset
uspto-grants-2014_08
Patent number
US08802698B2

Reaction notes

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