Ammonium Chloride → HCID 18546514, compound

HRID 1596314Notes

Reaction equation

HRID 1596314 reaction equation
CO[C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH:5]=[N:6][CH:7]([CH3:9])[CH3:8].Br[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[CH3:22].[Mg].[NH4+].[Cl-]>C1COCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[CH:5]=[N:6][CH:7]([CH3:9])[CH3:8])=[C:16]([CH3:22])[CH:17]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 967432-Bromo-5-fluorotolueneHCID 5462224MagnesiumHCID 10921064HCID 10921064, compound

Product 1

HCID 18546514HCID 18546514, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 14.57 g (81 mmol) N-(2-methoxybenzylidene)isopropylamin in 50 ml THF was added dropwise to a Grignard reagent prepared from 18.01 g (90 mmol) 2-bromo-5-fluorotoluene and 2.19 g (90 mmol) magnesium turnings in 50 ml THF. The mixture was heated at reflux for 12 hrs. The mixture was poured with vigorous stirring into an aqueous solution of NH4Cl (25%) and stirred for 1 h. Extraction with CH2Cl2, drying (Na2SO4) and evaporation gave 20.83 g (98%) (4′-fluoro-2′-methyl-biphenyl-2-ylmethylene)-isopropyl-amine as a pale yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 hrs
  3. additionThe mixture was poured
  4. extractionExtraction with CH2Cl2
  5. customdrying
  6. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-c9cd8dd7dced418d8f7116267a62dd0f
Source dataset
uspto-grants-2001_09
Patent number
US06291465B1

Reaction notes

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