Nitrogen → HCID 57755080, compound

HRID 1910104Notes

Reaction equation

HRID 1910104 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:20]=[C:21](O)[CH:22]=[C:23](Br)[CH:24]=1.[C:27]([O-:30])([O-])=O.[Na+].[Na+].N#N>C1(C)C=CC=CC=1.C(O)C.C(Cl)Cl.O>[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:10]3[CH:11]=[C:27]([OH:30])[CH:13]=[C:14]([C:24]4[CH:23]=[CH:22][C:21]([C:8]#[C:7][C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:20][CH:19]=4)[CH:9]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 947Nitrogen2×HCID 10340Sodium CarbonateHCID 122803,5-DibromophenolHCID 66774889HCID 66774889, compound

Product 1

HCID 57755080HCID 57755080, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
85 °C

Procedure

4-(Phenylethynyl)phenyl boronic acid (4.65 g, 20.9 mmol) was dissolved in 100 mL of toluene/ethanol (4:1 (v/v)), 3,5-dibromophenol (2.52 g, 10 mmol) was added, and then 20 mL of 2 M Na2CO3 (aqueous) was added. The resulting mixture was treated with 3 cycles of evacuation and refilling with N2. Solid tetrakis(triphenylphospine)palladium(II) (Pd(PPh3)4) (232 mg) was then added, followed by 3 more cycles of evacuation and refilling with N2. The reaction mixture was then heated to 85° C. in an oil bath for 5 hours. The reaction was cooled, and water (100 mL) and methylene chloride (100 mL) were added. The organic layer was separated, washed with water (50 mL), then dried (MgSO4), filtered, and evaporated. The crude product was purified by column chromatography (silica, CH2Cl2) or alternately by trituration with CH2Cl2 followed by filtration to give in either case about 2.5 g of the title compound as a white solid.

Workup

  1. temperatureThe reaction was cooled
  2. customThe organic layer was separated
  3. washwashed with water (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography (silica, CH2Cl2) or alternately by trituration with CH2Cl2
  8. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-94ea98c940bc464d9f348a23993759ba
Source dataset
uspto-grants-2013_12
Patent number
US08599673B2

Reaction notes

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