Hydrochloric Acid → 1-(3,5-Difluorophenyl)-4-pentylcyclohexan-1-OL

HRID 566156Notes

Reaction equation

HRID 566156 reaction equation
[Mg].Br[C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[CH:4]=1.[CH2:11]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)[CH2:12][CH2:13][CH2:14][CH3:15].Cl>C1COCC1>[OH:22][C:19]1([C:3]2[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[CH:4]=2)[CH2:20][CH2:21][CH:16]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5660974-PentylcyclohexanoneHCID 5462224Magnesium

Product 1

HCID 212653251-(3,5-Difluorophenyl)-4-pentylcyclohexan-1-OLYield 110%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of magnesium (600 mmol) and 1,300 ml of THF was added dropwise 1-bromo-3,5-difluorobenzene (500 mmol) at room temperature, and stirred at the same temperature for 30 min to prepare a Grignard reagent. To this solution was added dropwise a mixture of 4-pentylcyclohexanone (600 mmol) and 200 ml of THF, and stirred at the same temperature overnight. After 600 ml of 1N hydrochloric acid was added and stirred for 30 min, the reaction solution was extracted twice with diethyl ether and dried over anhydrous magnesium sulfate. The solvent was distilled off to give a (1-hydroxy-4-pentylcyclohexyl)-3,5-difluorobenzene (550 mmol). Purification was not particularly performed.

Workup

  1. additionTo this solution was added dropwise
  2. stirringstirred at the same temperature overnight
  3. stirringstirred for 30 min
  4. extractionthe reaction solution was extracted twice with diethyl ether
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9020a7c21a724341abac2eda7a6088d5
Source dataset
uspto-grants-2001_01
Patent number
US06174458B1

Reaction notes

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