Acetic Acid → HCID 18385778, compound

HRID 2298302Notes

Reaction equation

HRID 2298302 reaction equation
[CH2:1]([C:3]1([CH2:19][CH3:20])[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:25]Br>C(Cl)(Cl)Cl>[Br:25][C:6]1[C:7](=[O:8])[C:3]([CH2:1][CH3:2])([CH2:19][CH3:20])[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 18385981HCID 18385981, compound

Product 1

HCID 18385778HCID 18385778, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2,2-diethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (4.5 g) in 200 ml chloroform with 3 ml acetic acid, was added dropwise 1.5 ml bromine at 0° C. The solution was then allowed to warm to room temperature and was stirred for another 4 hours. The reaction was quenched by adding saturated aqueous sodium thiosulfate until the characteristic color of bromine disappeared. The reaction mixture was then extracted with dichloromethane (100 ml×2) and the organic layer was dried over anhydrous magnesium sulfate. After the magnesium sulfate was removed by filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by recrystallization from hexane and ethylacetate to afford 4.5 g of 4-bromo-2,2-diethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone. mp: 130-131° C. NMR: δ0.88 (t, J=7.5 Hz, 6H), 1.95 (q, J=7.5 Hz, 4H), 3.11 (s, 3H), 8.12 (d, J=8.7 Hz, 2H), 8.42 (d, J=8.7 Hz, 2H). IR (cm−1): 2973, 1705, 1583, 1558, 1315, 1160, 1084.

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated aqueous sodium thiosulfate until the characteristic color of bromine
  3. extractionThe reaction mixture was then extracted with dichloromethane (100 ml×2)
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customAfter the magnesium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting crude product was purified by recrystallization from hexane and ethylacetate

Sources & evidence

ORD record
ord-5411042aa60d4e94b83d02b21459d2cd
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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