Ethanol → HCID 178444292, compound

HRID 1936329Notes

Reaction equation

HRID 1936329 reaction equation
C(O)C.[CH2:4]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[CH2:5][CH2:6][CH2:7][CH3:8].Br[C:25]1[C:30]([F:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[C:27]([F:35])[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.CCOCC.O.C1C=CC=CC=1>[F:31][C:30]1[CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[C:27]([F:35])=[CH:26][C:25]=1[C:18]1[CH:17]=[CH:16][C:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:10][CH2:11]2)=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 178444242HCID 178444242, compound

Product 1

HCID 178444292HCID 178444292, compoundYield 84.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

First, 50 ml of ethanol containing 7.52 g of 4-(trans-4-pentylcyclohexyl)phenylboronic acid dissolved therein, 50 ml of benzene containing 5.0 g of 4-bromo-2,5-difluoro-1-nitrobenzene dissolved therein, 21.0 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.61 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 200 ml flask, and stirred under reflux for 12 hours. After the reaction, water and ether were added to the reaction solution for extraction. The resultant ether 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) and recrystallized from hexane, to obtain 6.87 g (Y: 84.4%) of 2,5-difluoro-4-nitro-4′-(trans-4-pentylcyclohexyl)biphenyl. The purity of the resultant compound was 100.0% as measured by GC. The phase transfer temperature of the compound was as follows.

Workup

  1. temperatureunder reflux for 12 hours
  2. additionwere added to the reaction solution for extraction
  3. washThe resultant ether layer was washed with a saturated brine
  4. dry with materialdried with sodium
  5. distillationThe solvent was then distilled off
  6. customThe residue was purified by silica gel column chromatography (eluent:toluene/hexane=1/4)
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-8d483aef38c74ad883007ade89a94893
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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