Iodine → HCID 18385599, compound

HRID 2298321Notes

Reaction equation

HRID 2298321 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3([CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:14](=[O:16])[CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].FC(F)(F)C(O[I:27](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.II>ClCCl>[I:27][C:15]1[C:14](=[O:16])[C:13]2([CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[O:12][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 18386141HCID 18386141, compound

Product 1

HCID 18385599HCID 18385599, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 2-{4-(methylsulfonyl)phenyl}-1,8-dioxa-spiro[4,5]dec-2-en-4-one (0.55 g), [bis(trifluoroacetoxy)iodo]benzene (0.84 g) and iodine (0.45 g) in 50 ml dichloromethane was stirred for 6 hours at room temperature. Then the reaction was quenched by adding 10 ml aqueous saturated sodium thiosulfate. The organic layer was washed with brine and was concentrated under reduced pressure. The resulting crude product was purified by column chromatography (hexane/ethylacetate) to afford 0.6 g of 3-iodo-2-{4-(methylsulfonyl)phenyl}-1,8-dioxa-spiro[4,5]dec-2-en-4-one. mp: 210-213° C. NMR: δ1.60-1.72 (m, 2H), 2.11-2.44 (m, 2H), 3.12 (s, 3H), 3.80-3.90 (m, 2H), 4.04-4.14 (m, 2H), 8.21 (d, J=9 Hz, 2H), 8.41 (d, J=9 Hz, 2H). IR (cm−1): 1690, 1580, 1146, 912, 744.

Workup

  1. customThen the reaction was quenched
  2. additionby adding 10 ml aqueous saturated sodium thiosulfate
  3. washThe organic layer was washed with brine
  4. concentrationwas concentrated under reduced pressure
  5. customThe resulting crude product was purified by column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-cf3c35b43ea24b2ebe5f5a5042184bb2
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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