Cyclopropanemethanol → HCID 57825256, compound

HRID 1668755Notes

Reaction equation

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

Participants

Reactant 3

HCID 75644Cyclopropanemethanol

HCID 2724254Sodium bis(trimethylsilyl)amide

HCID 27833303-Bromo-5-fluorobenzonitrile

Product 1

HCID 57825256HCID 57825256, compoundYield 84%

Procedure

In analogy to the procedure described in WO2007060448, the reaction of 3-bromo-5-fluorobenzonitrile with hydroxymethylcyclopropane using sodium bis(trimethylsilyl)amide as the base yielded the title compound as a white solid (yield: 84% of theory). TLC: Rf: 0.55 (silica gel:heptane:ethyl acetate=6:1, UV, 254 nm).

Sources & evidence

ORD record: ord-0f9656a425554dacb241589f91b332e3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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