2,6-Di-tert-butylphenol → HCID 66586998, compound

HRID 870116Notes

Reaction equation

HRID 870116 reaction equation
BrC1C=C[C:12]2[C:11]3[C:6](=CC(Br)=[CH:9][CH:10]=3)[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][Br:29])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Br:22])[C:4]=2C=1.[C:30]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36](C(C)(C)C)[C:35]=1O)([CH3:33])(C)C.[CH2:45](C([Sn])=C(CCCC)CCCC)[CH2:46]CC.[F-].[K+]>CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Br:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:5]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][Br:29])[C:35]2[CH:36]=[C:37]([CH:45]=[CH2:46])[CH:38]=[CH:39][C:34]=2[C:30]2[C:4]1=[CH:12][C:11]([CH:10]=[CH2:9])=[CH:6][CH:33]=2

Participants

8

Reactant 4

HCID 314052,6-Di-tert-butylphenolHCID 522689Potassium FluorideHCID 218679302,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluoreneHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 66586998HCID 66586998, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A flask with a stirring bar was charged with a mixture of compound 1 (1.000 g, 1.54 mmol), PdCl2(PPh3)2 (0.0588 g, 0.065 mmol), a few crystals of 2,6-ditert-butylphenol, and toluene (15.0 mL). The mixture was heated to 100° C. under nitrogen, and tributylvinyltin (1.125 g, 3.534 mmol) was added dropwise. The mixture was further heated for 23 hours. It was subsequently diluted with 60 mL of ether and treated with KF solution (˜10%). The mixture was stirred for 20 hours and followed by filtration to remove the insoluble solid. The organic layer was washed with water and dried over anhydrous MgSO4. After removal of the solvent, the residue was purified by column chromatography with n-hexane as eluent to afford 0.650 g of compound 2.

Workup

  1. temperatureThe mixture was further heated for 23 hours
  2. filtrationfollowed by filtration
  3. customto remove the insoluble solid
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography with n-hexane as eluent

Sources & evidence

ORD record
ord-4bbe3177a8784ef1a311010b986c19fd
Source dataset
uspto-grants-2015_03
Patent number
US08969509B2

Reaction notes

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