N-bromobutanimide → HCID 89648884, compound

HRID 1773961Notes

Reaction equation

HRID 1773961 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Br:15]N1C(=O)CCC1=O>CC#N>[Br:15][C:6]1[CH:7]=[C:8]([O:11][C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19013100HCID 19013100, compound

Product 1

HCID 89648884HCID 89648884, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of acetic acid 4-isopropoxy-phenyl ester (1.04 g, 5.35 mmol, 1 eq.) in MeCN (22 mL), N-bromsuccinimide (953 mg, 5.35 mmol, 1 eq.) was added. The resulting mixture was stirred at r.t. for 18 hours. The solvent was removed in vacuo. The residue was partitioned between water and Et2O. The org. layer was dried over MgSO4, filtered, and concentrated in vacuo to give acetic acid 3-bromo-4-isopropoxy-phenyl ester as an orange oil. The product was used without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned between water and Et2O
  3. dry with materiallayer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3efa6a6fa59d4fd9bb30ccd582eab252
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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