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

HRID 1399814Notes

Reaction equation

HRID 1399814 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Br[C:12]1[CH:17]=CC=C[C:13]=1[OH:18].CC(=O)OCC>CN(C=O)C.O>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:17][CH:12]1[CH2:13][O:18]1

Participants

7

Reactant 4

HCID 72442-BromophenolHCID 8857Ethyl AcetateHCID 115633-BromophenolHCID 24758Sodium hydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (416.2 mg, 17.34 mmol) in DMF (10 mL) was added 3-bromophenol (1.0 g, 5.78 mmol) at 9° C. and stirred for 5 minutes. To this mixture was added 2-bromophenol (1.2 g, 8.67 mmol) at 9° C. The reaction mixture was stirred for a further 16 h at 9° C. TLC (PE:EA=5:1) showed that the reaction was completed. The mixture was treated with water (50 mL) and extracted with EA (2×20 mL). The organic layer was washed with NaHCO3, brine (30 mL) then dried over Na2SO4 and concentrated to give 2-((3-bromophenoxy)methyl)oxirane (1.5 g, crude) as colorless oil which was used in next step without further purification. LCMS (m/z): 229.1/230.1 [M+H]+/[M+2H]+

Workup

  1. stirringThe reaction mixture was stirred for a further 16 h at 9° C
  2. extractionextracted with EA (2×20 mL)
  3. washThe organic layer was washed with NaHCO3, brine (30 mL)
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a368b1f6bf294c1fa5482e6234aafa9e
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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