Acetonitrile → HCID 19922010, compound

HRID 1647979Notes

Reaction equation

HRID 1647979 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOCC>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 19922010HCID 19922010, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.82 g (50 mmol) of 5-chlorosalicylaldehyde, 92.1 g (0.4 mol) of 1,5-dibromopentane, 22.1 g (0.15 mol) of anhydrous granular potassium carbonate, and 360 mL of acetonitrile was stirred and refluxed for 20 hr. The resulting slurry was cooled and diluted with 300 mL of ether. The solids were removed by suction filtration and washed thoroughly with ether. The filtrate and washes were combined and concentrated under water aspirator pressure. The excess 1,5-dibromopentane was removed by distillation under high vacuum. Flash chromatography of the residue on silica gel (eluting with 4:1 hexane-ether) afforded 12.5 g (81.8%) of 2-[(5-bromopentyl)oxy]-5-chlorobenzaldehyde as a yellow oil.

Workup

  1. temperaturerefluxed for 20 hr
  2. temperatureThe resulting slurry was cooled
  3. customThe solids were removed by suction filtration
  4. washwashed thoroughly with ether
  5. concentrationconcentrated under water aspirator pressure
  6. customThe excess 1,5-dibromopentane was removed by distillation under high vacuum

Sources & evidence

ORD record
ord-56551cee012d4a07904044048d8709da
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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