Toluene → HCID 86696071, compound

HRID 718498Notes

Reaction equation

HRID 718498 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)=[C:4]([F:19])[CH:3]=1.C1(C)C=CC=CC=1>[Pd].CC(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 86696069HCID 86696069, compound

Product 1

HCID 86696071HCID 86696071, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of compound (75) (75.0 g, 231.0 mmol) and 5%-palladium on carbon (0.5% sulfur, 50% water-containing article) (2.82 g, 3 wt %) was agitated for 18 hours under a hydrogen atmosphere in a toluene (300 mL)-IPA (100 mL) solvent. The reaction mixture was filtered and a solvent of a filtrate was distilled off by an evaporator. The residue was passed through silica gel column chromatography and recrystallized from heptane-ethanol, and thus 4-bromo-2-fluoro-1-(2-(4-propylcyclohexyl)ethyl)benzene (76) (57.1 g, yield 75.5%) was obtained.

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationa solvent of a filtrate was distilled off by an evaporator
  3. customrecrystallized from heptane-ethanol

Sources & evidence

ORD record
ord-cb32e2868c824a30b1a5373c3c30df4d
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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