Hydrochloric Acid → HCID 178447898, compound

HRID 1764993Notes

Reaction equation

HRID 1764993 reaction equation
[Mg].[F:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:4]=1Br.[CH2:12]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1)[CH2:13][CH3:14].Cl>C1COCC1.O>[F:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:4]=1[C:24]1([OH:27])[CH2:23][CH2:22][CH:21]([C@H:18]2[CH2:19][CH2:20][C@H:15]([CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17]2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27332551-Bromo-2,3,4-trifluorobenzeneHCID 5462224MagnesiumHCID 178447904HCID 178447904, compound

Product 1

HCID 178447898HCID 178447898, compoundYield 109.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Into 7.6 g of magnesium and 20 mL of THF which were stirred while water-cooling in a nitrogen atmosphere, a THF solution (200 mL) containing 60 g of 2,3,4-trifluorobromobenzene was added dropwise for 2 hours, and stirred for 3 hours. Into this, a THF solution (200 mL) containing 70 g of 4-(trans-4-propylcyclohexyl)cyclohexanone was added dropwise for 2 hours, and stirred for 2 hours. After the reaction solution was poured into 10% hydrochloric acid and stirred for a while, an organic layer was separated, and an aqueous layer was extracted with toluene. After the extract and the organic layer were mixed together, washed using water and a saturated saline solution in that order, and dried using anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure to obtain 110 g of 2,3,4-trifluoro-1-[1-hydroxy-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene (unsatisfactorily dried).

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. additionwas added dropwise for 2 hours
  3. additionwas added dropwise for 2 hours
  4. stirringstirred for 2 hours
  5. stirringstirred for a while
  6. customan organic layer was separated
  7. extractionan aqueous layer was extracted with toluene
  8. extractionAfter the extract
  9. additionthe organic layer were mixed together
  10. washwashed
  11. customa saturated saline solution in that order, and dried
  12. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-a928c8e2655f4eaf8fbae6173c5246f3
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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