Thiophene → 2-(4-Bromophenyl)thiophene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[S:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1>O.O.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[S:11][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
As shown in the following Reaction 8,130 mg (0.6 mmol) of 4-bromophenyl boronic acid was melted in 15 mL of thiophene, and 500 mg (3.22 mmol, 3 eq) of manganese(III) acetate dihydrate was added thereto, and then the reaction solution was refluxed for 1 hour at temperature of 85° C. Next, the reaction solution was filtered with hexane using a funnel charged with silica gel, and dehydrated with magnesium sulfate and distilled under reduced pressure. The compound distilled under reduced pressure was purified with a column chromatography (mobile phase: n-hexane) to obtain 140 mg of 2-(4-bromo-phenyl)-thiophene with a yield of 98%. NMR data of the obtained compound is as follows. [1H NMR (400 MHz, CDCl3): δ 7.50 (m, 4H), 7.25 (d, 2H), 7.07 (t, 1H)].
Workup
- filtrationNext, the reaction solution was filtered with hexane using a funnel
- additioncharged with silica gel
- distillationdistilled under reduced pressure
- distillationThe compound distilled under reduced pressure
- customwas purified with a column chromatography (mobile phase: n-hexane)
Sources & evidence
- ORD record
- ord-2766f26903b0406783ae131756eb9d55
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07850872B2
Reaction notes
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