Water → 1-(2-Bromoethyl)-4-(methoxymethyl)benzene

HRID 2360591Notes

Reaction equation

HRID 2360591 reaction equation
[H-].[Na+].[Br:3][CH2:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1.I[CH3:15].O>C1COCC1>[CH3:15][O:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([CH2:5][CH2:4][Br:3])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22337010[4-(2-Bromoethyl)phenyl]methanol

Product 1

HCID 201974281-(2-Bromoethyl)-4-(methoxymethyl)benzeneYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 60% NaH in paraffin (13.9 mmol; 0.56 g) in THF (20 ml) cooled to 0° C. was first added, dropwise, a solution of 4-(2-bromoethyl)benzyl alcohol (9.25 mmol; 1.99 g) in THF (20 ml) in an ice bath, followed by iodomethane (13.9 mmol; 1.972 g; 0.86 ml). The mixture was stirred at room temperature for 1 hour 30 minutes, after which it was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated NaCl solution (3×20 ml), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was chromatographed on a column of alumina, eluting with ethyl acetate, to give 1.38 g of product as an oil (65%).

Workup

  1. additionwas first added
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with saturated NaCl solution (3×20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on a column of alumina
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b97585ac876e4579915a94f0d0fadb0f
Source dataset
uspto-grants-2014_04
Patent number
US08686147B2

Reaction notes

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