Acetic Acid → 4-bromo-2-ethyl-2-methy-5-{4-(methylsulfonyl)-phenyl}-3(2H)-furanone

HRID 2298290Notes

Reaction equation

HRID 2298290 reaction equation
[CH2:1]([C:3]1([CH3:19])[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[O:4]1)[CH3:2].C(O)(=O)C.[Br:24]Br>C(Cl)(Cl)(Cl)Cl>[Br:24][C:6]1[C:7](=[O:8])[C:3]([CH2:1][CH3:2])([CH3:19])[O:4][C:5]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 183855812-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

Product 1

HCID 700020604-bromo-2-ethyl-2-methy-5-{4-(methylsulfonyl)-phenyl}-3(2H)-furanone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 4.5 g of 2-ethyl-2-methyl-5-{4-(methylsufonyl)phenyl}-3(2H)-furanone dissolved in 100 ml carbon tetrachloride, were added acetic acid (3 ml) and bromine (1 ml). The reaction solution was stirred for 1 hour at room temperature. Then the reaction was quenched by adding saturated aqueous sodium thiosulfate solution until the characteristic color of bromine disappeared. The reaction solution was extracted with dichloromethane (30 ml×3) and the organic layer was concentrated in vacuo. The resulting residue was purified by column chromatographic separation (hexane/ethylacetate=1:1) to give 4 g of 4-bromo-2-ethyl-2-methy-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone. NMR: δ0.91 (t, J=7.2 Hz, 3H), 1.52 (s, 3H), 1.95 (qd, J=7.2, 3.0 Hz, 2H), 3.11 (s, 3H), 8.11 (d, J=8.7 Hz, 2H), 8.41 (d, J=8.7 Hz, 2H). IR (cm−1): 2928, 1703, 1583, 1316, 1160, 552.

Workup

  1. customThen the reaction was quenched
  2. additionby adding saturated aqueous sodium thiosulfate solution until the characteristic color of bromine
  3. extractionThe reaction solution was extracted with dichloromethane (30 ml×3)
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThe resulting residue was purified by column chromatographic separation (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-fb70a1dcb1f74e0aa49fcc2a97fa03fb
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

Loading…