Acetonitrile → HCID 19922010, compound

HRID 327940Notes

Reaction equation

HRID 327940 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 10,225.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.82 g (50 mmol) of 5-chlorosalicylaldehyde, 92.1 g (0.4 mmol) 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 with 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. concentrationThe filtrate and washes with combined and concentrated under water aspirator pressure
  6. customThe excess 1,5-dibromopentane was removed by distillation under high vacuum

Sources & evidence

ORD record
ord-29f3c75ff5d448da8dd41b7b3cec22ef
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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