Toluene → 2,5-Dimethyl-4'-hexyloxybiphenyl

HRID 1635761Notes

Reaction equation

HRID 1635761 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1.[CH2:23]([O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>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.O>[CH3:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[C:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 11430Potassium CarbonateHCID 36821484-Hexyloxyphenylboronic Acid

Product 1

HCID 186766192,5-Dimethyl-4'-hexyloxybiphenyl

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Bromo-p-xylene (8.3 g, 45 mmol) (cf. A1 a)), K2CO3 (12.4 g, 90 mmol), 70 ml of toluene and 70 ml of H2O were placed in a reaction vessel and argon was passed in for 30 minutes. 4-hexyloxyphenylboronic acid (10 g, 45 mmol) and Pd(PPh3)4 (0.65 g, 0.56 mmol) were subsequently added under protective gas. The yellow-green, turbid mixture was stirred vigorously under a blanket of protective gas for about 20 hours at an internal temperature of 85° C. After phase separation, the organic phase was shaken with dilute HCl/H2O (until neutral). The aqueous phase was shaken with toluene and the organic phases were combined. After filtering off any palladium residues, the solution was evaporated. The crude product was purified by distillation under reduced pressure: the product was obtained as a yellow oil (boiling point: 117°-125° C./0.08 mbar): 10.3 g (81%). Purity>95% (1H-NMR).

Workup

  1. customwas passed in for 30 minutes
  2. customAfter phase separation
  3. stirringthe organic phase was shaken with dilute HCl/H2O (until neutral)
  4. stirringThe aqueous phase was shaken with toluene
  5. filtrationAfter filtering off any palladium residues
  6. customthe solution was evaporated
  7. distillationThe crude product was purified by distillation under reduced pressure
  8. customthe product was obtained as a yellow oil (boiling point: 117°-125° C./0.08 mbar)

Sources & evidence

ORD record
ord-28d132ad7a944018b7dc1ca657b3b54a
Source dataset
uspto-grants-2003_01
Patent number
US06509507B2

Reaction notes

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