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Toluene → HCID 15407951, compound

HRID 1107509
Notes
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Reaction equation

HRID 1107509 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11](Br)=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].[C:13]1(C)C=CC=C[CH:14]=1.C(C([SnH3])=C(CCCC)CCCC)CCC.[OH-].[Na+]>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.C(OCC)(=O)C>[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH:13]=[CH2:14])=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 110962627-BROMO-2,3-DIMETHYL-1-BENZOFURANHCID 21115800Tri(butyl)vinylstannane

Product 1

HCID 15407951HCID 15407951, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
2×
HCID 8857Ethyl AcetateSolvent

Procedure

32 g (142 mmol) of 2,3-dimethyl-7-bromobenzofuran, 3.3 g (2.84 mmol) of tetrakis(triphenylphosphine)palladium, 300 ml of toluene and 50 g (156.2 mmol) of tributylvinylstannane are introduced into a 1 liter three-necked flask equipped with a reflux condenser. The mixture is heated at reflux for 3 hours, 1 g of tetrakis(triphenylphosphine)palladium is added and heating is continued for 2 hours. The reaction mixture is allowed to return to room temperature and then 500 ml of ethyl acetate and 500 ml of aqueous sodium hydroxide solution are added. The organic phase is washed with brine, dried over magnesium sulphate and concentrated. The residue is distilled under a vacuum of 0.03 mm of Hg (4 Pa). The fraction distilling between 60 and 78° C. is collected and then purified by chromatography on a silica column (elution solvent: 1% ethyl acetate in cyclohexane). 23.5 g (Yield: 96%) of 2,3-dimethyl-7-ethenylbenzofuran are obtained in the form of a colourless oil.

Workup

  1. customequipped with a reflux condenser
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 3 hours
  4. temperatureheating
  5. customto return to room temperature
  6. washThe organic phase is washed with brine
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated
  9. distillationThe residue is distilled under a vacuum of 0.03 mm of Hg (4 Pa)
  10. distillationThe fraction distilling between 60 and 78° C.
  11. customis collected
  12. custompurified by chromatography on a silica column (elution solvent: 1% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-18f390beb1e34b2cabfa2c0e2a9143f5
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06060508

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes