Water → 4-Bromo-1-ethoxymethoxy-2-ethylbenzene

HRID 970831Notes

Reaction equation

HRID 970831 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[H-].[Na+].[CH2:13]([O:15][CH2:16]Cl)[CH3:14].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][O:15][CH2:13][CH3:14])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 179831144-Bromo-1-ethoxymethoxy-2-ethylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

24.5 g (121 mmol) of 4-bromo-2-ethylphenol are dissolved in 150 ml of DMF, and this solution is slowly added to a suspension of 5.3 g (133 mmol) of sodium hydride in 50 ml of DMF. The medium is stirred for 30 minutes, and then 12.4 ml (133 mmol) of ethoxymethyl chloride are added. The reaction medium is stirred for 4 hours at room temperature, and then poured into water and extracted with ethyl acetate. The organic phases are washed with water, and the residue obtained after drying and concentration is purified by chromatography on a silica column (eluent ethyl acetate 10/heptane 90). A yellow oil is obtained (m=25 g, y=80%)

Workup

  1. stirringThe reaction medium is stirred for 4 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phases are washed with water
  4. customthe residue obtained
  5. customafter drying
  6. concentrationconcentration
  7. customis purified by chromatography on a silica column (eluent ethyl acetate 10/heptane 90)
  8. customA yellow oil is obtained (m=25 g, y=80%)

Sources & evidence

ORD record
ord-faf6f1c761df4dbdbcb352058a3ae405
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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