2,2'-Dimethylbiphenyl → 2,2'-Dimethyl-5,5'-bis(1-adamantyl)biphenyl

HRID 41288

Reaction equation

HRID 41288 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].Br[C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2>[Fe](Cl)(Cl)Cl.[N+](C)([O-])=O>[CH3:14][C:9]1[CH:10]=[CH:11][C:12]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)=[CH:13][C:8]=1[C:3]1[CH:4]=[C:5]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 117972,2'-DimethylbiphenylHCID 791061-Bromoadamantane

Product 1

HCID 866419502,2'-Dimethyl-5,5'-bis(1-adamantyl)biphenylYield 48.2%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6375NitromethaneSolvent

Procedure

A 100 ml four-neck flask provided with a thermometer, stirrer, reflux tube, and nitrogen-introducing tube was charged with 2,2′-dimethylbiphenyl 14.7 g (80.55 mmol), 1-bromo-adamantane 34.7 g (161.1 mmol), and nitromethane 200 ml and the mixture stirred under a nitrogen flow at room temperature. Iron (III) chloride 1.31 g (8.07 mmol) was added and the result stirred at room temperature until dissolving. An oil bath was heated to 60° C., then the stirring was continued at that temperature for 4 hours. The reaction solution was filtered and rinsed away with a small amount of methanol. The filtered material was stirred in 30 ml of methanol for 30 minutes, then filtered. The obtained residue was dried at 60° C. under reduced pressure to obtain 2,2′-dimethyl-5,5′-bis(1-adamantyl)biphenyl white powder 17.5 g.

Workup

  1. customA 100 ml four-neck flask provided with a thermometer, stirrer
  2. temperaturereflux tube
  3. additionnitrogen-introducing tube
  4. stirringthe result stirred at room temperature
  5. dissolutionuntil dissolving
  6. temperatureAn oil bath was heated to 60° C.
  7. filtrationThe reaction solution was filtered
  8. washrinsed away with a small amount of methanol
  9. stirringThe filtered material was stirred in 30 ml of methanol for 30 minutes
  10. filtrationfiltered
  11. customThe obtained residue was dried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-5cb30b4366f44281b496e7a76d17fed4
Source dataset
uspto-grants-2013_09
Patent number
US08530596B2

Linked notes

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