Butyl bromide → HCID 19010186, compound

HRID 1741553Notes

Reaction equation

HRID 1741553 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[F:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[C:9]#[N:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:15][C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([F:6])[CH:14]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 19010186HCID 19010186, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1-bromobutane (18.0 g, 0.13 mol) in acetone (30 ml) was added dropwise to a stirred refluxing mixture of 2-fluoro-4-hydroxybenzonitrile (15.0 g, 0.11 mol) and potassium carbonate (46.0 g, 0.33 mol) in acetone (300 ml). The stirred mixture was heated under reflux for 21 h (glc analysis revealed absence of starting material). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water, 5% sodium hydroxide, water and dried (MgSO4). The solvent and the excess of 1-bromobutane were removed in vacuo to yield a pale-orange solid.

Workup

  1. temperaturerefluxing
  2. temperatureThe stirred mixture was heated
  3. temperatureunder reflux for 21 h (glc analysis revealed absence of starting material)
  4. extractionThe product was extracted into ether (twice), and the combined ethereal extracts
  5. washwere washed with water, 5% sodium hydroxide, water
  6. dry with materialdried (MgSO4)
  7. customThe solvent and the excess of 1-bromobutane were removed in vacuo
  8. customto yield a pale-orange solid

Sources & evidence

ORD record
ord-40ab283b9fb942b388ad75b7b4d13ab6
Source dataset
uspto-grants-1994_08
Patent number
US05334327

Reaction notes

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