Toluene → 1-(4-Bromophenyl)-2-methylpropan-2-ol

HRID 72959Notes

Reaction equation

HRID 72959 reaction equation
Br[Mg]C.[C:4]1(C)C=CC=CC=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]C(OCC)=O)=[CH:14][CH:13]=1.CC[O:26][CH2:27][CH3:28]>C1COCC1>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:27]([CH3:28])([OH:26])[CH3:4])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3283Diethyl Ether2×HCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 178418573HCID 178418573, compound

Product 1

HCID 3167851-(4-Bromophenyl)-2-methylpropan-2-olYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of bromo(methyl)magnesium in diethyl ether (25 mL of 3 M, 74.5 mmol) in THF (8 mL) and toluene (25 mL) was added to a solution of ethyl 2-(4-bromophenyl)acetate (8.23 g, 33.9 mmol) in Et2O (165 mL) and the reaction mixture was stirred at 40° C. for 1 hour. The reaction mixture was quenched by the addition of saturated aqueous ammonium chloride (200 mL) and the phases were separated. The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography eluting with 0-30% EtOAc-hexanes to give 1-(4-bromophenyl)-2-methyl-propan-2-ol (5.68 g, 73%), as a clear oil. ESI-MS m/z calc. 228.1. Found 229.5 (M+1)+; Retention time: 1.45 minutes (3 min run).

Workup

  1. customThe reaction mixture was quenched by the addition of saturated aqueous ammonium chloride (200 mL)
  2. customthe phases were separated
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with 0-30% EtOAc-hexanes

Sources & evidence

ORD record
ord-82f0ec2d64914cbabb059afa026c1533
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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