Hydrochloric Acid → HCID 20304310, compound

HRID 1732644Notes

Reaction equation

HRID 1732644 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:8])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1.Cl>C(OCC)C.O>[F:8][C:4]1[CH:3]=[C:2]([C:13]2([OH:17])[CH2:14][CH2:15][CH2:16][CH:11]([CH3:10])[CH2:12]2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115673-MethylcyclohexanoneHCID 140821-Bromo-3-fluorobenzeneHCID 5462224Magnesium

Product 1

HCID 20304310HCID 20304310, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
5 °C

Procedure

A solution of 50.0 g (0.28 mole) of 3-bromofluorobenzene in 100 ml of diethyl ether was added dropwise with stirring to a cooled reaction vessel containing 7.0 g (0.29 mole) of freshly dried magnesium turnings. The reaction began after 10-20% of the 3-bromofluorobenzene-ether solution had been added. The remainder of the addition was done at a rate sufficient to promote gentle reflux. Upon complete addition an additional 210 ml of diethyl ether was added and the reaction mixture was heated under reflux for 1 hour. The reaction mixture was cooled to 5° C. and 32.5 g (0.29 mole) of 3-methylcyclohexanone in 100 ml of diethyl ether was added dropwise during 30 minutes. Upon complete addition the reaction mixture was stirred for 1 hour at 5° C., heated to reflux temperature for 30 minutes, then allowed to cool to ambient temperature and stand for 16 hours. The reaction mixture was slurried in 450 ml of water and made acidic with aqueous 10% hydrochloric acid. The two phases were separated and the aqueous phase was extracted with three portions of diethyl ether. The combined ether extracts and organic phase were washed with two portions of a saturated aqueous solution of sodium bicarbonate, then one portion of water. The organic layer was dried with sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 58.0 g of 1-(3-fluorophenyl)-3-methyl-1-cyclohexanol as a solid. The compound was used without further purification.

Workup

  1. additionhad been added
  2. additionThe remainder of the addition
  3. additionwas added
  4. temperaturethe reaction mixture was heated
  5. temperatureunder reflux for 1 hour
  6. additionUpon complete addition the reaction mixture
  7. stirringwas stirred for 1 hour at 5° C.
  8. temperatureheated
  9. temperatureto reflux temperature for 30 minutes
  10. temperatureto cool to ambient temperature
  11. customThe two phases were separated
  12. extractionthe aqueous phase was extracted with three portions of diethyl ether
  13. washorganic phase were washed with two portions of a saturated aqueous solution of sodium bicarbonate
  14. dry with materialThe organic layer was dried with sodium sulfate
  15. filtrationfiltered
  16. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-178d9a891d4c4ec388e144e191682d41
Source dataset
uspto-grants-1980_12
Patent number
US04238505

Reaction notes

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