Ethanol → HCID 178444293, compound

HRID 1936327

Reaction equation

HRID 1936327 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]=[C:29]([F:31])[C:28](I)=[C:27]([F:33])[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]=[C:29]([F:31])[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:33])[CH:26]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27827025-Bromo-1,3-difluoro-2-iodobenzeneHCID 178444242HCID 178444242, compound

Product 1

HCID 178444293HCID 178444293, compoundYield 39.1%

Reagents, catalysts & solvents 4

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

Procedure

First, 50 ml of ethanol containing 5.61 g of 4-(trans-4-pentylcyclohexyl)phenylboronic acid dissolved therein, 50 ml of benzene containing 5.0 g of 4-bromo-2,6-difluoro-1-iodobenzene dissolved therein, 15.7 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.45 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 200 ml flask, and stirred under reflux for 48 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 2.58 g (Y: 39.1%) of 4-bromo-2,6-difluoro-4′-(trans-4-pentylcyclohexyl)biphenyl. The purity of the resultant compound was 100.0% as measured by GC. (5-b) Synthesis of polymerizable compound 2,6-difluoro-4′-(trans-4-pentylcyclohexyl)-4-vinylbiphenyl represented by formula (E) above

Workup

  1. temperatureunder reflux for 48 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-66da78fe7e7f4b39a300355dfbd4cd1d
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Linked notes

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