N-bromobutanimide → HCID 67461721, compound

HRID 2171208Notes

Reaction equation

HRID 2171208 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2[O:14][CH3:15])[CH2:3][CH2:2]1.[Br:16]N1C(=O)CCC1=O>C1COCC1>[Br:16][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[C:7]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67464460HCID 67464460, compound

Product 1

HCID 67461721HCID 67461721, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-(cyclopropylmethoxy)-1,3-dimethoxybenzene (500 mg, 2.40 mmol) in THF (25 mL) was added N-bromosuccinimide (430 mg, 2.40 mmol) and the resultant reaction mixture was stirred at RT for 4 h. The reaction mixture was concentrated under reduced pressure and the obtained residue was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 1-Bromo-3-(cyclopropylmethoxy)-2,4-dimethoxybenzene as a solid (500 mg, 73%).

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe obtained residue was diluted with water
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8031f07d6f04af9afa82a34e069b7a0
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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