Hydrochloric Acid → HCID 178445622, compound

HRID 1086765Notes

Reaction equation

HRID 1086765 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12](Cl)=[O:13])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].Br[C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=1.[Mg].Cl>O1CCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].O>[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)=[O:13])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 5462224MagnesiumHCID 178445624HCID 178445624, compound

Product 1

HCID 178445622HCID 178445622, compoundYield 58.5%

Reagents, catalysts & solvents 3

HCID 5483663Ferric acetylacetonateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Trans-4-butylcyclohexylacetyl chloride (25 g, 0.115 mol) was dissolved in dry tetrahydrofuran (30 ml), followed by cooling the solution down to 0° C., adding iron acetylacetonate (0.81 g), agitating the mixture, adding a solution of a Grignard reagent prepared from 1-bromo-3,4,5-trifluorobenzene (25 g, 0.115 mol) and metallic magnesium (2.8 g, 0.115 mol), in tetrahydrofuran, at a rate at which the reaction temperature did not exceed 10° C., reacting the mixture at 5° C. or lower for 2 hours, adding 6N hydrochloric acid (10 ml) and water (100 ml) to the reaction solution, extracting a deposited oily substance with n-heptane (100 m(), washing the extract solution with a dilute alkali aqueous solution, washing with water till the washing water became neutral, drying over anhydrous sodium sulfate, distilling off n-heptane from the n-heptane solution, and recrystallizing the residue from ethyl alcohol to obtain 1-(trans-4butylcyclohexylacetyl)-3,4,5-trifluorobenzene (21.0 g). C-I point: 42.8° C. This compound was dissolved in ethyl acetate (100 ml), followed by adding 5% Pd supported on barium sulfate (0.5 g), subjecting the mixture to a catalytic reduction at 25° C. under 3 atm till hydrogen absorption ceased, filtering off the catalyst after completion of the reaction, and subjecting the reaction solution to a suitable purification treatment to obtain 1-(trans-4-butylcyclohexyl)-2-(3,4,5-trifluorophenyl)ethane (18.0 g). C-I point: 8.4° C.

Workup

  1. customdid not exceed 10° C.
  2. customat 5° C.
  3. extractionextracting a deposited oily substance with n-heptane (100 m(),
  4. washwashing the extract solution with a dilute alkali aqueous solution
  5. washwashing with water till the washing water
  6. dry with materialdrying over anhydrous sodium sulfate
  7. distillationdistilling off n-heptane from the n-heptane solution
  8. customrecrystallizing the residue from ethyl alcohol

Sources & evidence

ORD record
ord-f0e69e67e3b14125a14ce7aa8f6324dd
Source dataset
uspto-grants-1991_07
Patent number
US05032313

Reaction notes

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