4-Bromo-2-fluorobenzonitrile → HCID 22461737, compound

HRID 1937777Notes

Reaction equation

HRID 1937777 reaction equation
F[C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][C:12]([CH3:15])([O-:14])[CH3:13].[K+]>C1COCC1>[C:12]([O:14][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])([CH3:15])([CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 7360294-Bromo-2-fluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 22461737HCID 22461737, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-4-bromobenzonitrile (2.0 g, 10 mmol) in 10 mL of THF, cooled to −15° C., was added a solution of potassium t-butoxide (10 mL, 10 mmol) over 7 min. The cooling bath was removed, and the reaction stirred for another 40 min. The reaction was poured into ether/10% HCl, and the ether layer was separated. The ether layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated to give 2.5 g of 2-t-butoxy-4-bromobenzonitrile.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was poured into ether/10% HCl
  3. customthe ether layer was separated
  4. washThe ether layer was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2cd9698260804ceabbf7e60577ce4932
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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