Toluene → HCID 3358921, compound

HRID 852085Notes

Reaction equation

HRID 852085 reaction equation
Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.C1(C)C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>CO.CCOCC.CCCCCCC.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>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[S:5][CH:6]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 3

HCID 1140TolueneHCID 123250Benzo(b)thiophene, 3-bromo-HCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 3358921HCID 3358921, compoundYield 83.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8900HeptaneSolvent

Procedure

Mix 3-bromobenzo[b]thiophene (5.83 g, 27.4 mmol), tetrakis(triphenylphosphine)palladium (O) (1.00 g, 0.865 mmol) and toluene (60 mL) and purge with nitrogen. Rapidly, add a 2 M aqueous solution of sodium carbonate (27 mL) and purge with nitrogen. Add a solution of 4-methoxyphenylboronic acid (4.57 g, 30.1 mmol) in methanol (13 mL), purge with nitrogen and heat at a gentle reflux for 4.5 hours. Let cool and stir at room temperature, overnight. TLC (30% dicloromethane in heptane) shows that all starting material is consumed. Dilute reaction mixture with ethyl acetate (100 mL). Wash with 2 M sodium carbonate (75 mL), water (75 mL), saturated sodium chloride (75 mL), dry (MgSO4) and concentrate (in vacuo) to give a residue. Purify the residue by column (silica) chromatography (20% dichloromethane in heptane) to give a mixture as a residue. Dissolve the residue in 30% ether in heptane, filter, evaporate and dry (0.5 mm Hg, room temperature) to give the title compound as a clear oil (5.47 g, 83% Yield).

Workup

  1. custompurge with nitrogen
  2. additionRapidly, add a 2 M aqueous solution of sodium carbonate (27 mL)
  3. custompurge with nitrogen
  4. custompurge with nitrogen
  5. temperatureheat at
  6. temperaturea gentle reflux for 4.5 hours
  7. temperatureLet cool
  8. customis consumed
  9. additionDilute
  10. customreaction mixture with ethyl acetate (100 mL)
  11. washWash with 2 M sodium carbonate (75 mL), water (75 mL), saturated sodium chloride (75 mL)
  12. dry with materialdry (MgSO4)
  13. concentrationconcentrate (in vacuo)
  14. customto give a residue
  15. customPurify the residue by column (silica) chromatography (20% dichloromethane in heptane)
  16. customto give a mixture as a residue
  17. filtrationfilter
  18. customevaporate
  19. customdry (0.5 mm Hg, room temperature)

Sources & evidence

ORD record
ord-feac39420d9b4def9e113e1257339100
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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