Acetic Acid → 2-(4-Fluorophenyl)thiophene
Reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.C(O)(=O)C>O>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:2]2[S:3][CH:4]=[CH:5][CH:6]=2)=[CH:10][CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2 °C
Procedure
2-Bromothiophene (130.4 g, 0.8 mol) was dissolved in 2-Me-THF (240 ml, 0.3 L/mole) and the resulting mixture cooled to 2° C. NiCl2(dppe) (2.11 g, 4.0 mmol) was added followed by addition, over about 40 min. at ≦30° C., of the 4-fluoro-phenylmagnesium bromide solution prepared as in STEP A above to yield a dark red solution. The solution was then stirred at 22° C. for 1.5 hrs. A solution of acetic acid (91.7 ml, 1.6 mol) in water (240 ml, 0.3 L/mol) was then added and the resulting mixture stirred strongly for 15 min. The resulting layers were separated, the organic layer was washed with water (80 ml, 0.1 L/mol), then concentrated in vacuo at 75° C. to yield 2-(4-fluorophenyl)thiophene as a brown oil.
Workup
- customto yield a dark red solution
- stirringthe resulting mixture stirred strongly for 15 min
- customThe resulting layers were separated
- washthe organic layer was washed with water (80 ml, 0.1 L/mol)
- concentrationconcentrated in vacuo at 75° C.
Sources & evidence
- ORD record
- ord-6a3a30a9ba0649169a5867463e8443db
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056850B2
Reaction notes
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