Hydrochloric Acid → 1-Bromo-4-(ethoxymethyl)benzene

HRID 2175384Notes

Reaction equation

HRID 2175384 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.I[CH2:13][CH3:14].Cl>CN(C)C=O>[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:9][CH2:13][CH3:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 5981871-Bromo-4-(ethoxymethyl)benzeneYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaOH (0.1 g, 2.4 mmol) was added to 2 ml of degassed dimethylformamide and 4-bromobenzylalcohol (0.3 g, 1.6 mmol) was further added slowly. Iodoethane (0.14 ml, 1.76 mmol) was added at room temperature followed by stirring for 2 hours. The mixture was added with 50 ml of 2N c HCl and extracted with 50 ml of ethylacetate. The organic layer was washed twice with 50 ml of H2O. After concentration under vacuum and column chromatography (ethylacetate/n-hexane, 1/10), the title compound (0.17 g, 48%) was obtained as yellowish oil.

Workup

  1. additionwas further added slowly
  2. extractionextracted with 50 ml of ethylacetate
  3. washThe organic layer was washed twice with 50 ml of H2O
  4. concentrationAfter concentration under vacuum and column chromatography (ethylacetate/n-hexane, 1/10)

Sources & evidence

ORD record
ord-d6fd1e9f94e54d5abd4a6f0cc620c5b8
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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