Methanol → HCID 23445636, compound

HRID 1280922Notes

Reaction equation

HRID 1280922 reaction equation
F[B-](F)(F)F.[Br:6][C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([N+]#N)=[C:9]([CH2:17][CH3:18])[CH:8]=1.[CH3:19][OH:20]>[Cl-].[Zn+2].[Cl-]>[Br:6][C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([O:20][CH3:19])=[C:9]([CH2:17][CH3:18])[CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 234456594-Bromo-2,6-diethylbenzenediazonium Tetrafluoroborate

Product 1

HCID 23445636HCID 23445636, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A stirred solution containing 4-bromo-2,6-diethylbenzenediazonium tetrafluoroborate (17.25 g, 52.77 mmol) and freshly ground anhydrous zinc chloride (7.2 g, 52.9 mmol) in methanol (1.06 L) was refluxed for 6 h. The reaction was cooled to ambient temperature, quenched with H2O (1.2 L), saturated with solid sodium chloride and extracted with hexane. The combined organic extracts were sequentially washed with sat. aq. NaHCO3 (1×100 mL), with H2O (1×100 mL), with brine (1×100 mL), dried (Na2SO4) and concentrated to give 12.0 g (94%) of title compound. 1H NMR: consistent. mass spectrum (EI), m/z 242 (M+).

Workup

  1. temperaturewas refluxed for 6 h
  2. customquenched with H2O (1.2 L), saturated with solid sodium chloride
  3. extractionextracted with hexane
  4. washThe combined organic extracts were sequentially washed with sat. aq. NaHCO3 (1×100 mL), with H2O (1×100 mL), with brine (1×100 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41075c0d9c104d99992eeecd73329d62
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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