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

HRID 2422518Notes

Reaction equation

HRID 2422518 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:18])[CH:8]=1)(=O)=O.[Br:21]N1C(=O)CCC1=O.C1(C)C=CC=CC=1.C1C[O:39][CH2:38][CH2:37]1.O>>[Br:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([C:38](=[O:39])[CH2:37][Br:21])=[CH:8][C:9](=[O:18])[O:10]2)=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 194269487-bromo-2-oxo-2H-chromen-4-yl trifluoromethanesulfonateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

Procedure

To a solution of 7-bromo-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate (2.71 g, 9.35 mmol) in THF-water (40 mL, 10/1 mixture), N-bromosuccinimide (1.83 g, 10.3 mmol) was added. The reaction was then stirred at room temperature. After 5 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, 25:75) to afford the title compound. 1H NMR (400 MHz, acetone-d6 7.80 (d, 1H), 7.72-7.62 (m, 1H), 7.60 (d, 1H), 7.13 (s, 1H), 4.92 (s, 2H).

Workup

  1. stirringAfter 5 hours stirring
  2. customthe crude mixture was evaporated under reduced pressure
  3. customThe crude residue obtained
  4. customwas purified by column chromatography (EtOAc/hexanes, 25:75)

Sources & evidence

ORD record
ord-9c0f20d52da3479da74c727019529127
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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