Sodium Carbonate → 4-(4-Bromophenyl)dibenzo[b,d]furan

HRID 900331Notes

Reaction equation

HRID 900331 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][C:21](I)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.[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>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([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:20][CH:19]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 590220984-(4-Bromophenyl)dibenzo[b,d]furan

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 mL) was added to a stirred solution of 1-bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis-(triphenylphosphine)-palladium(0) (271 mg, 5 mol %) in toluene (40 mL). 2 N sodium carbonate (4.7 mL, 9.4 mmol) was added and then the reaction was heated to 90° C. (oil bath temp.) for 2-3 h until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2×20 mL). The combined organic extracts were washed with water and sat'd aq NaCl. The ethereal solution was dried over anhyd MgSO4, filtered and concentrated in vacuo to yield 4-(4-bromophenyl)-dibenzofuran as a yellow solid, which was used immediately without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and diethyl ether
  3. customThe phases were separated
  4. extractionthe aqueous phase being further extracted with diethyl ether (2×20 mL)
  5. washThe combined organic extracts were washed with water
  6. dry with materialThe ethereal solution was dried over anhyd MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c725ac4a80e64d79853d3d1b1801eba1
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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