Toluene → HCID 19366437, compound

HRID 849434Notes

Reaction equation

HRID 849434 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][CH:7]=1.[Mg].[O:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>Cl.C(CC(=O)C)(=O)C.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([C:14](=[O:10])[CH2:13][CH:12]2[CH2:19][CH2:20][CH:15]([CH2:16][CH2:17][CH3:18])[CH2:21][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8028Tetrahydrofuran2×HCID 140821-Bromo-3-fluorobenzeneHCID 5462224Magnesium

Product 1

HCID 19366437HCID 19366437, compound

Reagents, catalysts & solvents 2

HCID 86755040HCID 86755040, compoundCatalystHCID 313Hydrochloric AcidSolvent

Procedure

Grignard's reagent prepared from 3-fluorobromobenzene (110 mmol), magnesium (110 mmol), and 100 ml of tetrahydrofuran (hereinafter referred to as THF) was added dropwise to a mixture prepared by adding iron acetylacetone (5 mmol) and 300 ml of dried toluene to the acid chloride (100 mmol) at a temperature lower than -50° C. and stirred for 1 hour at the same temperature. The reaction product thus obtained was added in 200 ml of 6M hydrochloric acid and then extracted with toluene (100 ml×2). Extract was dried with anhydrous magnesium sulfate, the solvent was distilled off, and the residue thus obtained was recrystallized from 50 ml of ethanol to obtain 2-fluoro-4-(1-oxo-2-(4-propylcyclohexyl)ethyl)benzene (75 mmol).

Workup

  1. additionwas added dropwise to a mixture
  2. customprepared
  3. customThe reaction product thus obtained
  4. extractionextracted with toluene (100 ml×2)
  5. extractionExtract
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customthe residue thus obtained
  9. customwas recrystallized from 50 ml of ethanol

Sources & evidence

ORD record
ord-d733ee8ceb75458cacd6bf4bcd909deb
Source dataset
uspto-grants-2000_01
Patent number
US06013198

Reaction notes

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