Bromide ion → HCID 59518034, compound

HRID 2363210Notes

Reaction equation

HRID 2363210 reaction equation
[Mg].II.Br[CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7].[Br-].[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][CH:15]=1>C1COCC1>[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([OH:21])[CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 259Bromide ionHCID 807IodineHCID 124151-Bromo-2,2-dimethylpropaneHCID 15294Methyl 4-FormylbenzoateHCID 5462224Magnesium2×

Product 1

HCID 59518034HCID 59518034, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Magnesium (5.2 g, 199 mmol) is suspended in anhydrous THF (60 mL) under nitrogen. A small crystal of iodine is added. 1-Bromo-2,2-dimethylpropane (25 g, 165 mmol) is dissolved in anhydrous THF (90 mL) and a portion of the solution is added to the magnesium. The mixture is heated to reflux temperature to initiate the reaction. The rest of the bromide solution is added dropwise. After the addition is complete the mixture is refluxed for 4 h. The Grignard reagent is allowed to cool to room temperature and added dropwise to a solution of methyl-4-formylbenzoate (15 g, 91.5 mmol) in THF which has been cooled in an ice bath. After the addition is complete the resulting solution is stirred at room temperature for 2 h. The reaction is quenched with MeOH, worked up and concentrated to give 8.07 g (37%) of the titled compound as a yellow oil. 1H NMR.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. customthe reaction
  4. additionAfter the addition
  5. temperatureis refluxed for 4 h
  6. temperaturehas been cooled in an ice bath
  7. additionAfter the addition
  8. customThe reaction is quenched with MeOH
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-36708236ef8b4dc387693df198da5447
Source dataset
uspto-grants-2014_04
Patent number
US08691856B2

Reaction notes

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