Water → [2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanol

HRID 505659Notes

Reaction equation

HRID 505659 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.[Br:17]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:17][C:6]1[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][C:9]([O:11][CH2:12][O:13][CH3:14])=[CH:8][C:7]=1[CH2:15][OH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 104437513,5-Bis(methoxymethoxy)benzylalcohol

Product 1

HCID 10957768[2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanolYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The above-obtained 3,5-bis(methoxymethoxy)phenylmethanol (5.3 g, 23 mmol) was dissolved in N,N-dimethylformamide (20 mL) and obtained solution was added with N-bromosuccinimide (4.3 g, 24 mmol) followed by stirring at a room temperature for 5 hours. The reaction mixture was added with water and extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 5/1 to 2/1) to obtain [2-bromo-3,5-bis(methoxymethoxy)phenyl]methanol (4.9 g, 69%).

Workup

  1. customobtained solution
  2. extractionextracted with chloroform 3 times
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 5/1 to 2/1)

Sources & evidence

ORD record
ord-b4b9bcf5be70400bb0382abde22e2ca3
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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