Methanol → HCID 23445636, compound

HRID 1067359Notes

Reaction equation

HRID 1067359 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, compound

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 tide 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
  7. customto give 12.0 g (94%) of tide compound

Sources & evidence

ORD record
ord-15f49f8b600e4b8fbc9906674f6b96b7
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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