Trimethylsilylacetylene → Tert-butyl{4-cyano-2-[(trimethylsilyl)ethynyl]phenoxy}acetate

HRID 2390144Notes

Reaction equation

[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](Cl)=[CH:11][C:10]=1[C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)COC1C=CC([C:37]#[N:38])=CC=1Br)(C)(C)C.C[Si](C#C)(C)C>>[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:37]#[N:38])=[CH:11][C:10]=1[C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 66111Trimethylsilylacetylene

HCID 56594380Tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate

HCID 58521856Tert-butyl 2-(2-bromo-4-cyanophenoxy)acetate2×

Product 1

HCID 58521908Tert-butyl{4-cyano-2-[(trimethylsilyl)ethynyl]phenoxy}acetateYield 87%

Procedure

Following the general method as outlined in Intermediate 2, starting from tert-butyl(2-bromo-4-cyanophenoxy)acetate (Intermediate 44) and (trimethylsilyl)acetylene (Aldrich), the title compound was obtained as a dark brown sticky solid in 87% yield.

Sources & evidence

ORD record: ord-47256b9790624be4800c2434eaef6e3f
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273769B2

Reaction notes

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