Benzonitrile, 4-bromo- → 4-Cyanophenol

HRID 1424754Notes

Reaction equation

I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.BrC1C=CC(C#N)=CC=1.[OH-:19].[Cs+]>>[OH:19][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 12162Benzonitrile, 4-bromo-

HCID 62750Cesium hydroxide

HCID 764674-Iodobenzonitrile

Product 1

HCID 130194-Cyanophenol

Procedure

Following general operating mode A, 4-iodobenzonitrile or 4-bromobenzonitrile (229 mg or 182 mg, 1.0 mmol) were reacted at respectively 110° C. or 130° C. with cesium hydroxide to afford the expected product in the form of a white solid at respective yields of 91% and 94% (eluent: ethyl acetate/heptane 20:80).

Sources & evidence

ORD record: ord-1bd47fa599c047eab048a27a9190d4f3
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927779B2

Reaction notes

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