Tetrabutylammonium Fluoride → 2-(4-Bromofuran-2-yl)pyridine

HRID 2109465Notes

Reaction equation

HRID 2109465 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1([Si](C)(C)C)[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[O:22][CH2:21]1>O1CCCC1>[Br:19][C:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[O:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69053979HCID 69053979, compound

Product 1

HCID 576342462-(4-Bromofuran-2-yl)pyridineYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Tetra-n-butylammonium fluoride (1M in tetrahydrofuran, 25.1 mL, 25.11 mmol) was added to a solution of 3-bromo-5-(2-pyridyl)-3-(trimethylsilyl)furan (4.96 g, 16.74 mmol) in tetrahydrofuran (50 mL). The reaction mixture was heated at 70° C. (bath temperature) for six hours. The reaction mixture was evaporated, and the residue was purified by flash chromatography using hexane as the eluant to give the sub-title compound as a pale brown solid (3.02 g), m/z 224, 226 (MH+).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5659b7f3f12649d9bc3bd7bf643c97f9
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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