Ethanol → HCID 178444285, compound

HRID 1936335Notes

Reaction equation

HRID 1936335 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].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:32]=[C:31](Br)[CH:30]=[CH:29][C:27]=1[NH2:28].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>[NH2:28][C:27]1[CH:29]=[CH:30][C:31]([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:32][C:26]=1[C:25]([F:35])([F:34])[F:24]

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 679604-Bromo-2-(trifluoromethyl)anilineHCID 178444242HCID 178444242, compound

Product 1

HCID 178444285HCID 178444285, compoundYield 91.3%

Reagents, catalysts & solvents 4

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

Procedure

First, 100 ml of ethanol containing 4.91 g of 4-(trans-4-pentylcyclohexyl)phenylboronic acid dissolved therein, 100 ml of benzene containing 10.0 g of 2-trifluoromethyl-4-bromoaniline, 41.7 ml of a sodium carbonate aqueous solution with a concentration of 2 mol/l, and 1.20 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 300 ml flask, and stirred under reflux for six 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/toluene=4/1), to obtain 14.82 g (Y: 91.3%) of 4-amino-4′-(trans-4-pentylcyclohexyl)-3-trifluoromethylbiphenyl. The purity of the resultant compound was 99.2% as measured by GC.

Workup

  1. temperatureunder reflux for six 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/toluene=4/1)

Sources & evidence

ORD record
ord-6023d2a2f0a1473fb5c137087a94bba9
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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