2-Bromothiophene → 2-[(Trimethylsilyl)ethynyl]thiophene

HRID 911559Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7]([Si:9]([CH3:12])([CH3:11])[CH3:10])#[CH:8]>>[CH3:10][Si:9]([CH3:12])([CH3:11])[C:7]#[C:8][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 138512-Bromothiophene

HCID 66111Trimethylsilylacetylene

Product 1

HCID 5968702-[(Trimethylsilyl)ethynyl]thiopheneYield 81%

Procedure

Use a method similar to the General Procedure 8 to couple 2-bromo-thiophene (0.97 nm, 10 mmol) with ethynyl-trimethylsilane (2.82 mL, 20 mmol). Purify by chromatography on silica gel eluting with isohexane to give the desired intermediate (1.46 g, 81%). GC-MS m/z 180 (M+).

Workup

customPurify by chromatography on silica gel eluting with isohexane

Sources & evidence

ORD record: ord-93017a89bd9b4668b40f9cbd73af4b99
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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