Sodium Carbonate → 2-(4-Fluorophenyl)thiophene

HRID 2271012Notes

Reaction equation

HRID 2271012 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.Br[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1>O.C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 138512-BromothiopheneHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 218947832-(4-Fluorophenyl)thiopheneYield 96.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of sodium carbonate (1.63 g) in H2O (7.65 ml), 4-fluorobenzeneboronic acid (1.03 g) and tetrakis(triphenylphosphine) palladium(0) (70.9 mg) were added successively to a solution of 2-bromothiophene (1.00 g) in dimethoxyethane (12.3 ml). The mixture was refluxed for 4 hours. The mixture was cooled to ambient temperature and partitioned between AcOEt and H2O. The organic layer was washed with 0.5N aqueous NaOH solution and saturated aqueous NaCl solution, dried over MgSO4 and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: n-hexane and then AcOEt in n-hexane 10%). The solvent was evaporated in vacuo to give 1.05 g of 2-(4-fluorophenyl)thiophene as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. custompartitioned between AcOEt and H2O
  3. washThe organic layer was washed with 0.5N aqueous NaOH solution and saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 column chromatography (eluent
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-87852ba9af824dd18457fc37a6b0979f
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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