4-Cyanophenol → 4-((5-Chloropentyl)oxy)benzonitrile

HRID 1925578Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Cl:16]>>[Cl:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 130194-Cyanophenol

HCID 960701-Bromo-5-chloropentane

Product 1

HCID 193815104-((5-Chloropentyl)oxy)benzonitrile

Procedure

In step 1-1, 4-hydroxy-benzonitrile (2; R4=H, X3=O) is reacted with 1-bromo-5-chloropentane (3; Br—X2—Cl: X2=pentylene), giving 4-(5-chloro-pentoxy)-benzonitrile (4). The reaction temperature is preferably maintained in the range of 10 to 90° C., for 1 to 9 hours and the reaction solvent is acetonitrile, dimethylformamide, etc. To ensure that the above reaction occurs under a basic condition, an inorganic basic compound such as potassium carbonate, sodium hydroxide, sodium hydride, etc, may be used.

Sources & evidence

ORD record: ord-450c6d40caa94902a1f1f018415a5b0f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178688B2

Reaction notes

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