Tetrahydrofuran → HCID 87924367, compound

HRID 1358740Notes

Reaction equation

HRID 1358740 reaction equation
[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[CH2:13]1[CH2:17]O[CH2:15][CH2:14]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:9]=[CH:8][C:7]([C:15]#[C:14][C:13]2[CH:17]=[CH:9][C:4]([S:3][C:2]([F:12])([F:11])[F:1])=[CH:5][CH:6]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 7364134-(Trifluoromethylthio)bromobenzene

Product 1

HCID 87924367HCID 87924367, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 4-(trifluoromethylthio)bromobenzene (0.47 g, 1.82 mmol), bis (tri-N-butylstannyl)acetylene (0.5 g, 0.83 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.05 g, 0.04 mmol) in THF (10 mL) under nitrogen was heated to reflux overnight. After the usual work-up, it was purified by column chromatography to give 0.24 g (80%) of 1,2-bis(4-trifluoromethylthiophenyl)acetylene as a white fluffy solid. 1HNMR (360 MHz, DMSO-d6) δ7.72-7.79 (m, 8H). MS-EI m/z 378 [M+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customAfter the usual work-up, it was purified by column chromatography

Sources & evidence

ORD record
ord-57726c2d725c46f189041fd94f551342
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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