Ethyl Acetate → HCID 67463851, compound

HRID 1616212Notes

Reaction equation

HRID 1616212 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])C(OC)=O.[CH3:13][Mg]Br.C([O:19][CH2:20][CH3:21])(=O)C>C1COCC1.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([C:20]([OH:19])([CH3:21])[CH3:13])[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 7015747Methyl 3-bromo-4-methylbenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 67463851HCID 67463851, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-78 °C

Procedure

To a round bottom flask, Methyl 3-bromo-4-methylbenzoate (25 g, 109 mmol) was added under nitrogen, dissolved in THF (110 mL), and cooled to −78° C. 3M methylmagnesium bromide (85 ml, 251 mmol) was added slowly to the cooled solution and allowed to stir for 30 minutes. The reaction was warmed to room temperature for 30 minutes until complete conversion over starting material. The solution was diluted with ethyl acetate and sodium bicarbonate. Extracted (3×) with ethyl acetate, and washed the combined organic layers with brine, dried over sodium sulfate, filtered, and concentrated to afford the desired 2-(3-bromo-4-methylphenyl)propan-2-ol (3-1). MS (M+H)+: observed=211.0/213.0, calculated=211.1/213.1.

Workup

  1. temperatureThe reaction was warmed to room temperature for 30 minutes until complete conversion
  2. extractionExtracted (3×) with ethyl acetate
  3. washwashed the combined organic layers with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9c8e41416f7648089384dae92ae3f67e
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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