Ethanol → HCID 178444249, compound

HRID 1936326Notes

Reaction equation

HRID 1936326 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:24][C:25]1[CH:30]=[CH:29][C:28](I)=[C:27]([F:32])[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>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([C:18]2[CH:17]=[CH:16][C:15]([C@H:12]3[CH2:13][CH2:14][C@H:9]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:10][CH2:11]3)=[CH:20][CH:19]=2)=[C:27]([F:32])[CH:26]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 178444242HCID 178444242, compound

Product 1

HCID 178444249HCID 178444249, compoundYield 67.8%

Reagents, catalysts & solvents 4

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

Procedure

First, 150 ml of ethanol containing 17.84 g of 4-(trans-4-pentylcyclohexyl)phenylboronic acid dissolved therein, 150 ml of benzene containing 15.0 g of 4-bromo-2-fluoro-1-iodobenzene dissolved therein, 49.8 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 1.44 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 500 ml flask, and stirred under reflux for 37 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:hexane) and recrystallized from hexane, to obtain 13.6 g (Y: 67.8%) of 4-bromo-2-fluoro-4′-(trans-4-pentylcyclohexyl)biphenyl. The purity of the resultant compound was 99.5% as measured by GC.

Workup

  1. temperatureunder reflux for 37 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 sulfate
  5. distillationThe solvent was then distilled off
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane)
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-d9d84a9bfcfb4e82a69dd50494d0e44c
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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