Hydrochloric Acid → HCID 178447829, compound

HRID 857602Notes

Reaction equation

HRID 857602 reaction equation
[Li].[F:2][C:3]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](Br)=[CH:8]2.I[C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.Cl>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.C1COCC1>[F:2][C:3]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:16]1[CH:17]=[CH:18][C:19]([C@H:22]3[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]3)=[CH:20][CH:21]=1)=[CH:8]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3028194LithiumHCID 114138325,6-Difluoro-2-bromonaphthaleneHCID 178447892HCID 178447892, compound

Product 1

HCID 178447829HCID 178447829, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF solution of an organic lithium reagent prepared from 5,6-difluoro-2-bromonaphthalene were added dropwise 4-iodo-1-(trans-4-propylcyclohexyl)benzene and a THF solution of tetrakis(triphenylphosphine)palladium (0) in the catalytic amount. The reaction mixture was then stirred at room temperature for 3 hours. To the reaction mixture were then added water and toluene to terminate the reaction. To the reaction solution was then added diluted hydrochloric acid until the aqueous phase became weakly acidic. The reaction solution was then extracted with toluene. The material thus extracted and the organic phase were together washed with water and then with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain an oily matter. The oily matter was purified through silica gel column chromatography (hexane), and then recrystallized from ethanol to obtain 5,6-difluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene in the form of white crystal.

Workup

  1. customadded water and toluene to terminate
  2. customthe reaction
  3. extractionThe reaction solution was then extracted with toluene
  4. extractionThe material thus extracted
  5. washthe organic phase were together washed with water
  6. dry with materialwith saturated brine, and then dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto obtain an oily matter
  9. customThe oily matter was purified through silica gel column chromatography (hexane)
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d5b64def43d848078631c8d3994f0c1f
Source dataset
uspto-grants-2006_12
Patent number
US07145047B2

Reaction notes

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