Benzene → HCID 22465765, compound

HRID 1936333Notes

Reaction equation

HRID 1936333 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[C:20](=[O:23])([O-])[O-].[Na+].[Na+].O>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.C1(C)C=CC=CC=1>[CH2:20]([O:23][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 10340Sodium CarbonateHCID 907181-Bromo-4-cyclohexylbenzene

Product 1

HCID 22465765HCID 22465765, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

First, 80 ml of ethanol containing 7.18 g of 4-benzyloxyphenylboronic acid obtained from the synthesis (10-b) above dissolved therein, 50 ml of benzene containing 5.00 g of 1-bromo-4-cyclohexylbenzene dissolved therein, 21.0 ml of a sodium carbonate aqueous solution with a concentration of 2 mol/l, and 0.24 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 200 ml flask, and stirred under reflux for eight hours. After the reaction, water and toluene were added to the reaction solution for extraction. The resultant toluene layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography (eluent:toluene/hexane=1/4), to obtain 5.04 g (Y: 70.1%) of 4-benzyloxy-4′-cyclohexylbiphenyl. The purity of the resultant compound was 98.3% as measured by GC.

Workup

  1. dissolutionabove dissolved
  2. temperatureunder reflux for eight hours
  3. additionwere added to the reaction solution for extraction
  4. washThe resultant toluene layer was washed with a saturated brine
  5. dry with materialdried with sodium sulfate
  6. distillationThe solvent was then distilled off
  7. customThe residue was purified by silica gel column chromatography (eluent:toluene/hexane=1/4)

Sources & evidence

ORD record
ord-34ebe43f9cfa49b2923455301b5f0ba1
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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