Toluene → HCID 22045224, compound

HRID 1830489Notes

Reaction equation

HRID 1830489 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([C:11]1[C:23](OB(O)O)=[CH:22][C:21]2[C:20]3[C:15](=[C:16]([F:28])[CH:17]=[CH:18][CH:19]=3)[CH2:14][C:13]=2[C:12]=1[F:29])[CH2:9][CH3:10].IC1C=CC(C)=CC=1.C(=O)([O-])[O-].[Na+].[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(O)C>[CH3:7][C:1]1[CH:6]=[CH:5][C:4]([C:17]2[C:16]([F:28])=[C:15]3[C:20]([C:21]4[CH:22]=[CH:23][C:11]([CH2:8][CH2:9][CH3:10])=[C:12]([F:29])[C:13]=4[CH2:14]3)=[CH:19][CH:18]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 122074-IodotolueneHCID 69531289HCID 69531289, compound

Product 1

HCID 22045224HCID 22045224, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To 200 ml of toluene was added 8.2 g of (2-propyl-1,8-difluorofluorenyl)boric acid (K-5), 7.4 g of p-iodotoluene, 31 ml of 2M aqueous sodium carbonate, 0.5 ml of ethanol and 1.0 g of tetrakis(triphenylphosphine)palladium, and the mixture was refluxed under heat for 20 hours. The reaction mixture was then washed sequentially with water and a saturated aqueous solution of sodium chloride, dried, and then purified by silica gel chromatography to yield 7.1 g of 7-(4-methylphenyl)-2-(n-propyl)-1,8-difluorofluorene (II-I1).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 20 hours
  3. washThe reaction mixture was then washed sequentially with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-cb7a26c031364e9593f54ec8edc0b08c
Source dataset
uspto-grants-2006_06
Patent number
US07067179B1

Reaction notes

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