Hydrochloric Acid → HCID 86630166, compound

HRID 251712Notes

Reaction equation

HRID 251712 reaction equation
[Mg].[C:2]12([C:12]3[CH:13]=[CH:14][C:15](Br)=[C:16]([CH3:18])[CH:17]=3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:20]12([C:30]3[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=3)[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2.Cl>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.O1CCCC1>[C:2]12([C:12]3[CH:13]=[CH:14][C:15]([C:33]4[CH:32]=[CH:31][C:30]([C:20]56[CH2:21][CH:22]7[CH2:28][CH:26]([CH2:25][CH:24]([CH2:23]7)[CH2:29]5)[CH2:27]6)=[CH:35][CH:34]=4)=[C:16]([CH3:18])[CH:17]=3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6259221-(4-Bromophenyl)adamantaneHCID 5462224MagnesiumHCID 67505817HCID 67505817, compound

Product 1

HCID 86630166HCID 86630166, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

In a 1 L recovery flask, 3.19 g of magnesium (131 mmol), g of 5-(1-adamantyl)-2-bromotoluene (131 mmol), 200 mL of tetrahydrofuran and a stirrer were charged and refluxed under a nitrogen atmosphere for two hours to prepare a Grignard reagent. Next, in another 1 L recovery flask, 38.2 g of 4-(1-adamantyl)-bromobenzene (131 mmol), 9.19 mg of bis(triphenylphosphine)palladium dichloride (13.1 mmol), 300 mL of tetrahydrofuran and a stirrer were charged. A tetrahydrofuran solution, which is the above-prepared Grignard reagent, was added thereto under nitrogen flow and the mixture was refluxed for 12 hours. Then, 60 mL of 10% hydrochloric acid aqueous solution was added thereto and the mixture was refluxed for 30 minutes. After an aqueous layer was separated and removed therefrom, the reaction solution was washed with 200 mL of saturated sodium hydrogencarbonate aqueous solution, followed by removal of solvent under reduced pressure. Solid thus obtained was refined by alumina column chromatography, thus obtaining 45.1 g of 4,4′-di(1-adamantyl)-2-methyl-1,1′-biphenyl (103.5 mmol; yield: 79.0%).

Workup

  1. additionwere charged
  2. temperaturerefluxed under a nitrogen atmosphere for two hours
  3. additionwas added
  4. temperatureunder nitrogen flow and the mixture was refluxed for 12 hours
  5. temperaturethe mixture was refluxed for 30 minutes
  6. customAfter an aqueous layer was separated
  7. customremoved
  8. washthe reaction solution was washed with 200 mL of saturated sodium hydrogencarbonate aqueous solution
  9. customfollowed by removal of solvent under reduced pressure
  10. customSolid thus obtained

Sources & evidence

ORD record
ord-558ec4e7f1fa439bade69b6162bb1c1a
Source dataset
uspto-grants-2011_01
Patent number
US07863347B2

Reaction notes

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