Potassium Carbonate → 1-ethynyl-2,4,5-trifluorobenzene

HRID 1929978Notes

Reaction equation

HRID 1929978 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=1[F:13].C([O-])([O-])=O.[K+].[K+]>CO>[C:4]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=1[F:13])#[CH:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57929980HCID 57929980, compound

Product 1

HCID 228979761-ethynyl-2,4,5-trifluorobenzeneYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trimethyl((2,4,5-trifluorophenyl)ethynyl)silane (10 g, 46 mmol, prepared using General Procedure J from 1-bromo-2,4,5-trifluorobenzene and ethynyltrimethylsilane), K2CO3 (0.64 g, 4.6 mmol) and MeOH (25 mL) was stirred at ambient temperature for about 3.5 h. The reaction was quenched with water and extracted with Et2O. The organic layer was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using pentane as eluent to give the title compound as oil (1.5 g, 21% yield): LC/MS (Table 1, Method a) Rt=3.58 min; 1H NMR (CDCl3) 3.38 (s, 1 H), 7.00-7.06 (m, 1 H), 7.35-7.40 (m, 1 H). Additional product (5.6 g, ˜40% purity, ˜33%) was recovered from rotary evaporator condenser.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with Et2O
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a06377d9eb72428d84d93e4fc125074c
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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