Sodium Carbonate → HCID 59855508, compound
Reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](I)[CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:17][C:18]1[CH:19]=[C:20]([C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH:21]=[CH:22][CH:23]=1Participants
9
Reactant 3
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 4-dibenzofuranboronic acid (51 mmol), 1-Bromo-3-iodo-benzene (51 mmol), and Pd(PPh3)4, (4 mmol) in 250 mL of toluene and 150 mL of ethanol was heated to obtain a clear solution, then Na2CO3 (155 mmol) in 250 mL water was added. The reaction mixture refluxed for 4 h at 80° C. The mixture was cooled to room temperature and diluted with 300 mL ethyl acetate. The organic layer was washed with 2×300 mL portions of water, 2×300 mL portions of sat. aq. NaCl, and dried (MgSO4). After the solution was concentrated, the residue was purified by column chromatography (eluted with 2% EtOAc-Heptane) to afford 4-(3-Bromo-phenyl)-dibenzofuran.
Workup
- temperaturewas heated
- customto obtain a clear solution
- temperatureThe mixture was cooled to room temperature
- washThe organic layer was washed with 2×300 mL portions of water, 2×300 mL portions of sat. aq. NaCl
- dry with materialdried (MgSO4)
- concentrationAfter the solution was concentrated
- customthe residue was purified by column chromatography (eluted with 2% EtOAc-Heptane)
Sources & evidence
- ORD record
- ord-2cedbaf4b2594034ab946f7c953de0a0
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498356B2
Reaction notes
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