Acetonitrile → 7-Iodobenzofuran-5-sulfonyl chloride

HRID 1162035Notes

Reaction equation

HRID 1162035 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N(Br)C(=O)C1.[I:21][C:22]1[C:30]2[O:29][CH2:28][CH2:27][C:26]=2[CH:25]=[C:24]([S:31]([Cl:34])(=[O:33])=[O:32])[CH:23]=1.C(#N)C>ClC1C=CC=CC=1>[I:21][C:22]1[C:30]2[O:29][CH:28]=[CH:27][C:26]=2[CH:25]=[C:24]([S:31]([Cl:34])(=[O:32])=[O:33])[CH:23]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 534309327-Iodo-2,3-dihydrobenzofuran-5-sulfonyl chloride2×

Product 1

HCID 534029757-Iodobenzofuran-5-sulfonyl chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

AIBN (270 mg, 1.3 mmol) and NBS (2.5 g, 14 mmol) were added to 7-iodo-2,3-dihydro-benzofuran-5-sulfonyl chloride (4.4 g, 13 mmol; Intermediate 55) in chlorobenzene (30 mL) at 70° C. The heating was turned off one hour after the addition. Acetonitrile (30 mL) was added and the organic phase was washed with sodium sulphite in water. The organic phase was separated and the volatiles were evaporated to give 4 g (90%) of the title compound as yellow crystals. 1H NMR 270 MHz (CDCl3) δ ppm 7.07 (d, J=2.23 Hz, 1H) 7.90 (d, J=2.23 Hz, 1H) 8.29-8.37 (m, 1H).

Workup

  1. additionafter the addition
  2. washthe organic phase was washed with sodium sulphite in water
  3. customThe organic phase was separated
  4. customthe volatiles were evaporated

Sources & evidence

ORD record
ord-65685197f9e04014aba6dfbd8b3a05a6
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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