Acetonitrile → 7-Iodo-2,3-dihydrobenzofuran-5-sulfonyl chloride

HRID 1162034Notes

Reaction equation

HRID 1162034 reaction equation
[I:1]Cl.[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:11][C:6]=2[CH2:5][CH2:4]1.C(#N)C>C(Cl)Cl>[I:1][C:8]1[C:7]2[O:3][CH2:4][CH2:5][C:6]=2[CH:11]=[C:10]([S:12]([Cl:15])(=[O:13])=[O:14])[CH:9]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24640Iodine chlorideHCID 27761542,3-Dihydrobenzofuran-5-sulfonyl Chloride2×

Product 1

HCID 534309327-Iodo-2,3-dihydrobenzofuran-5-sulfonyl chlorideYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ICl (7.7 g, 47 mmol) in DCM (100 mL) was added dropwise to a solution of 2,3-dihydro-benzofuran-5-sulfonyl chloride (5 g, 23 mmol; Intermediate 54) in DCM (100 mL) at reflux temperature under nitrogen atmosphere. The reaction was heated at reflux overnight. The reaction mixture was cooled at room temperature and acetonitrile (50 mL) was added. The resultant mixture was washed with a saturated solution of NaHCO3 and the organic phase was separated followed by elimination of the volatiles under vacuum to give 8 g of brown oil which was used to the next step without further purification. 1H NMR 270 MHz (CDCl3) δ ppm 3.45 (t, J=8.91 Hz, 2H) 4.82 (t, J=8.91 Hz, 2H) 7.79 (d, J=1.48 Hz, 1H) 8.16 (d, J=1.98 Hz, 1H).

Workup

  1. temperatureat reflux temperature under nitrogen atmosphere
  2. temperatureThe reaction was heated
  3. temperatureat reflux overnight
  4. washThe resultant mixture was washed with a saturated solution of NaHCO3
  5. customthe organic phase was separated

Sources & evidence

ORD record
ord-7ac2232947d141388d89e4f30606268d
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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