Methyl iodide → 1-Bromo-4-(1-methoxy-2-methylpropan-2-yl)benzene

HRID 1043495Notes

Reaction equation

HRID 1043495 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.I[CH3:14].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][O:10][CH3:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128051244-Bromo-beta,beta-dimethylbenzeneethanol

Product 1

HCID 102434781-Bromo-4-(1-methoxy-2-methylpropan-2-yl)benzeneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the material from Step 2 (500 mg, 2.18 mmol) in 8 mL of DMF was added iodomethane (0.68 mL, 10.9 mmol) and NaH (60% in oil, 131 mg, 3.28 mmol). The mixture was stirred at room temperature for 2 h. The reaction was quenched with water, and extracted with EtOAc and hexane. The organic layer was separated, washed with saturated sodium bicarbonate, dried over MgSO4, and concentrated. The crude was purified by flash silica column (eluting with 5% EtOAc in hexane) to get 1-bromo-4-(1-methoxy-2-methylpropan-2-yl)benzene (460 mg, 87%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc and hexane
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude was purified by flash silica column (eluting with 5% EtOAc in hexane)

Sources & evidence

ORD record
ord-a69c2774eca340ad87fa687cc17552df
Source dataset
uspto-grants-2013_10
Patent number
US08563543B2

Reaction notes

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