Trimethylsilylacetylene → (2-Nitro-4-trimethylsilanylethynyl-phenyl)-carbamic acid tert.-butyl ester

HRID 1745469Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16])([CH3:4])([CH3:3])[CH3:2].[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 23554339Tert-butyl (4-iodo-2-nitrophenyl)carbamate

Product 1

HCID 67289195(2-Nitro-4-trimethylsilanylethynyl-phenyl)-carbamic acid tert.-butyl esterYield 107.6%

Procedure

Prepared from (4-iodo-2-nitro-phenyl)-carbamic acid tert.-butyl ester (Example A1) (3.64 g, 10 mmol) and trimethylsilylacetylene (4.2 mL, 30 mmol) according to the general procedure F. Obtained as a green oil (3.6 g).

Sources & evidence

ORD record: ord-b2ad639086d6411d8206fe331b1e528e
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07018998B2

Reaction notes

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