2-Chlorobenzaldehyde → HCID 21933582, compound

HRID 1370164Notes

Reaction equation

HRID 1370164 reaction equation
CNCCN(C)C.[CH2:8]([Li])[CH2:9][CH2:10]C.[Cl:13][C:14]1[C:19]([CH:20]=[O:21])=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cu]C#N.C(Br)C=C.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:10]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:13])[C:19]=1[CH:20]=[O:21])[CH:9]=[CH2:8]

Participants

9

Reactant 6

HCID 69962-ChlorobenzaldehydeHCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 178418339Butyllithium2×HCID 178418546HCID 178418546, compound

Product 1

HCID 21933582HCID 21933582, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of protective gas, a solution of 10.89 g (0.107 mol) of trimethylethylenediamine in 50 ml of anhydrous tetrahydrofuran was cooled to −10° C. and mixed dropwise with 66.6 ml of a 1.6 molar n-butyllithium solution in hexane (0.107 mol). After 10 minutes, 15 g (0.107 mol) of 6-chlorobenzaldehyde in 70 ml of tetrahydrofuran were added dropwise, and the mixture was admixed with a further 0.214 mol of n-butyllithium in hexane (146.8 ml) and stirred at 0° C. for 2.5 hours. The mixture was cooled to −20° C., 12.42 g (0.139 mol) of copper(I) cyanide were added, the mixture was stirred at −10° C. for 30 minutes and 28.42 g of allyl bromide in 100 ml of tetrahydrofuran were then added dropwise. Stirring was continued at 0° C. for 2.5 hours, and 230 ml of saturated ammonium chloride solution were then added dropwise. The resulting solid was separated off and the aqueous phase was extracted with diethyl ether. The combined organic phases were then washed with saturated ammonium chloride solution and dried, and the solvent was removed under reduced pressure. This gave 17.0 g of 2-alkyl-6-chlorobenzaldehyde [sic] (89%) in the form of a dark oil.

Workup

  1. temperatureThe mixture was cooled to −20° C.
  2. stirringthe mixture was stirred at −10° C. for 30 minutes
  3. stirringStirring
  4. waitwas continued at 0° C. for 2.5 hours
  5. customThe resulting solid was separated off
  6. extractionthe aqueous phase was extracted with diethyl ether
  7. washThe combined organic phases were then washed with saturated ammonium chloride solution
  8. customdried
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b526cdf2da54b0caf3ffb33fda6b644
Source dataset
uspto-grants-2003_06
Patent number
US06583089B1

Reaction notes

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