N-bromobutanimide → HCID 67061224, compound

HRID 506190Notes

Reaction equation

HRID 506190 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].[Br:17]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Br:17][C:10]1[CH:9]=[CH:8][C:7]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 33045771,2-BIS(2-MEO-ETO)BENZENE

Product 1

HCID 67061224HCID 67061224, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2-Bis(2-methoxyethoxy)benzene (8.1 g, 31.9 mmol) and N-bromosuccinimide (6.2 g, 35 mmol) were stirred in 50 mL DMF at room temperature overnight. The reaction was diluted with 200 mL EtOAc and washed with 1N NaOH and water. The organic layer was dried over magnesium sulfate and concentrated to give 9.7 g (92%) of 4-bromo-1,2-bis(2-methoxyethoxy)benzene.

Workup

  1. washwashed with 1N NaOH and water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6055e416fc634130b6a5999500db282f
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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