Ethanol → 4-Methylbiphenyl

HRID 368916Notes

Reaction equation

HRID 368916 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13]C=[CH:11][CH:10]=1.[C:18](=O)([O-])[O-].[Na+].[Na+].C(O)C>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.COCCOC>[CH3:18][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 78054-BromotolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid

Product 1

HCID 125664-MethylbiphenylYield 55%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

Table 1, Entry 10. In the reaction tube were mixed 4-bromotoluene (0.171 g, 1.0 mmol), phenylboronic acid (0.134 g, 1.1 mmol), Pd(PPh3)4 (0.0347 g, 0.030 mmol), sodium cabonate (0.212 g, 2.0 mmol), 0.187 ml 95% ethanol, 0.375 ml water and 0.75 ml DME.under nitrogen. The contents of the flask were irradiated for 2.50 min with an effect of 55 W. After cooling, the product mixture was poured into 25 ml water and was extracted three times with 25 ml DCM. The combined extracts were washed with 25 ml saline and concentrated to an oil. The crude product was purified by column chromatography on silica gel using i-hexane as the eluent. The yield was 55% (white solid).

Workup

  1. customThe contents of the flask were irradiated for 2.50 min with an effect of 55 W
  2. temperatureAfter cooling
  3. extractionwas extracted three times with 25 ml DCM
  4. washThe combined extracts were washed with 25 ml saline
  5. concentrationconcentrated to an oil
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-67d8364b52cc4fc8a0be1a70511f9cf5
Source dataset
uspto-grants-2000_10
Patent number
US06136157

Reaction notes

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