Ethanol → HCID 178444250, compound

HRID 1936328Notes

Reaction equation

HRID 1936328 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)=[CH:27][C:26]=1[F:32].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)=[CH:27][C:26]=1[F:32]

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 178444242HCID 178444242, compound

Product 1

HCID 178444250HCID 178444250, compoundYield 86.8%

Reagents, catalysts & solvents 4

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

Procedure

First, 100 ml of ethanol containing 11.89 g of 4-(trans-4-pentylcyclohexyl)phenylboronic acid dissolved therein, 100 ml of benzene containing 10.0 g of 1-bromo-2-fluoro-4-iodobenzene dissolved therein, 33.2 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.96 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 500 ml flask, and stirred under reflux for 16 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 acetone, to obtain 11.6 g (Y: 86.8%) of 4-bromo-3-fluoro-4′-(trans-4-pentylcyclohexyl)biphenyl. The purity of the resultant compound was 100.0% as measured by GC.

Workup

  1. temperatureunder reflux for 16 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 acetone

Sources & evidence

ORD record
ord-47fd2f373537462184625effcc4d8eb4
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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