Acetic Acid → HCID 18385639, compound

HRID 2298304Notes

Reaction equation

HRID 2298304 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3([CH2:18][CH2:17][CH2:16][CH2:15]3)[C:12](=[O:14])[CH:13]=2)=[CH:5][CH:4]=1.[Br:19]Br.C(O)(=O)C>C(Cl)(Cl)(Cl)Cl>[Br:19][C:13]1[C:12](=[O:14])[C:11]2([CH2:15][CH2:16][CH2:17][CH2:18]2)[O:10][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 18385721HCID 18385721, compound

Product 1

HCID 18385639HCID 18385639, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 147 mg of 2-{4-(methylthio)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one in 30 ml carbon tetrachloride, were added 1 ml bromine and 0.1 ml acetic acid. The reaction mixture 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 quenched solution was extracted with dichloromethane (10 ml×3). The organic layer was concentrated under reduced pressure and the resulting residue was purified by column chromatography (hexane/ethylacetate) to yield 50 mg of 3-bromo-2-{4-(methylthio)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one. NMR: δ1.98 (m, 4H), 2.11 (m, 4H), 2.55 (s, 3H), 7.32 (d, J=8.7 Hz, 2H), 8.13 (d, J=8.7 Hz, 2H).

Workup

  1. customThen the reaction was quenched
  2. additionby adding saturated aqueous sodium thiosulfate solution until the characteristic color of bromine
  3. extractionThe quenched solution was extracted with dichloromethane (10 ml×3)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was purified by column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-c9c94e5dee6d446bbbcd0be337b2498e
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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