Water → 1-(4-Chloro-2-formyl-phenoxymethyl)-cyclopropanecarbonitrile

HRID 504528Notes

Reaction equation

HRID 504528 reaction equation
[C:1]([C:3]1([CH2:6]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:5][CH2:4]1)#[N:2].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([OH:27])=[C:23]([CH:26]=1)[CH:24]=[O:25].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:27][CH2:6][C:3]2([C:1]#[N:2])[CH2:5][CH2:4]2)=[C:23]([CH:24]=[O:25])[CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 22028201(1-Cyanocyclopropyl)methyl 4-methylbenzenesulfonate

Product 1

HCID 577501451-(4-Chloro-2-formyl-phenoxymethyl)-cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude toluene-4-sulfonic acid 1-cyano-cyclopropylmethyl ester in DMF (30 mL) was added 5-chloro-2-hydroxy-benzaldehyde (5.9 g, 38 mmol) and K2CO3 (10.5 g, 76 mmol) slowly. The reaction mixture was placed in a sealed tube and irradiated by microwave reactor at 75° C. for 30 min. After cooled to room temperature, the mixture was poured into water. The solution was diluted with EtOAc (200 mL), washed with water, dried and concentrated to give the title compound as a black oil (4.76 g). The oil was used for next step reaction directly without further purification.

Workup

  1. customThe reaction mixture was placed in a sealed tube
  2. customirradiated by microwave reactor at 75° C. for 30 min
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a0235571d0f3488a98e5788f096107ce
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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