Water → 2-[(3-Bromophenoxy)methyl]oxirane

HRID 1399832Notes

Reaction equation

HRID 1399832 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Br[CH2:12][CH:13]1[CH2:15][O:14]1.O>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][CH:13]1[CH2:15][O:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 115633-BromophenolHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 38653422-[(3-Bromophenoxy)methyl]oxiraneYield 113.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of compound NaH (416.2 mg, 17.34 mmol) in DMF (10 mL) was added 3-bromophenol (1.0 g, 5.78 mmol) at 20° C. After addition the solution was stirred for 5 minutes at this temperature before the addition of 2-(bromomethyl)oxirane (1.2 g, 8.67 mmol). The reaction mixture was stirred for 16 h at 20° C. Once complete the reaction mixture was treated with water (50 mL) and extracted with EA (2×20 mL) and the organic layers combined and washed with NaHCO3, brine (30 mL), dried over Na2SO4 and concentrated to give the compound 2-((3-bromophenoxy)methyl)oxirane (1.5 g, crude) as colorless oil which was used in next step without further purification.

Workup

  1. additionAfter addition the solution
  2. extractionextracted with EA (2×20 mL)
  3. washwashed with NaHCO3, brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c36ef686203b46e098d17c307c600010
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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