Toluene → 4-(bromoacetyl)-7-methyl-2H-chromen-2-one

HRID 2422515Notes

Reaction equation

HRID 2422515 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[O:9][C:8](=[O:17])[CH:7]=1)=[CH2:5])C.[Br:18]N1C(=O)CCC1=O.C1(C)C=CC=CC=1>C1COCC1.O>[Br:18][CH2:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[O:9][C:8](=[O:17])[CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 597748944-(1-ethoxyvinyl)-7-methyl-2H-chromen-2-one

Product 1

HCID 866219744-(bromoacetyl)-7-methyl-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-(1-ethoxyvinyl)-7-methyl-2H-chromen-2-one (1.56 g, 6.77 mmol) in THF-water (27.5 mL, 10/1 mixture), N-bromosuccinimide (1.33 g, 7.45 mmol) was added. The reaction was then stirred at room temperature. After 3 hours stirring, toluene was added and the crude mixture was evaporated under reduced pressure. The crude residue obtained was purified by column chromatography (EtOAc/hexanes, 30:70) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.71 (d, 1H), 7.24 (s, 1H), 7.22 (d, 1H), 6.94 (s, 1H), 4.90 (s, 2H), 2.50 (s, 3H).

Workup

  1. stirringAfter 3 hours stirring
  2. customthe crude mixture was evaporated under reduced pressure
  3. customThe crude residue obtained
  4. customwas purified by column chromatography (EtOAc/hexanes, 30:70)

Sources & evidence

ORD record
ord-17c3b63a53fa4b75aed1ba06f33ac336
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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