N-bromobutanimide → 4-bromo-5-methoxy-2,3-dihydro-1H-inden-1-one

HRID 471434Notes

Reaction equation

HRID 471434 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[Al].[Br:14]N1C(=O)CCC1=O>O>[Br:14][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:12]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 787875-Methoxyindan-1-oneHCID 5359268Aluminum

Product 1

HCID 378189874-bromo-5-methoxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Methoxy-indane-1-one (17.2 g, 106.05 mmol) is suspended in 100 mL of water. The flask is covered with an aluminium foil to create a dark environment. N-Bromo-succinimide (18.87 g, 106.05 mmol) is added portionwise and the reaction mixture is stirred at room temperature overnight. The reaction mixture is extracted with 200 mL of ethyl acetate, the organic phase is collected, dried over sodium sulfate and concentrated under vacuum. The crude product obtained (20 g) is used in the next step without any further treatment.

Workup

  1. extractionThe reaction mixture is extracted with 200 mL of ethyl acetate
  2. customthe organic phase is collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cba5939f0b054985826a413ac0332291
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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