Chlorosulfonic acid → 2-Ethylbenzo[b]furan-3-sulfonyl chloride

HRID 1166928Notes

Reaction equation

HRID 1166928 reaction equation
[CH2:1]([C:3]1[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1)[CH3:2].[Cl:12][S:13](O)(=[O:15])=[O:14].P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([C:3]1[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[C:4]=1[S:13]([Cl:12])(=[O:15])=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 765822-Ethylbenzofuran

Product 1

HCID 229984082-Ethylbenzo[b]furan-3-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Ethylbenzo[b]furan-3-sulfonyl chloride was prepared by the method of Example 82C with 2-ethylbenzo[b]furan (6.9 mmols, 1.0 g), chlorosulfonic acid (8.9 mmols, 0.6 ml) phosphorus oxychloride (21 mmols, 1.9 ml), phosphorus pentachloride (6.9 mmols, 1.4 g) and CH2Cl2 (10 ml). Flash chromatography (2% ethyl acetate/hexanes) provided 0.71 g (42%) of an orange solid.

Sources & evidence

ORD record
ord-33c935a134a84fdc9cbeb014e6cab646
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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