4-Fluoroanisole → 5-Fluoro-2-methoxybenzene-1-sulfonyl chloride

HRID 1971833Notes

Reaction equation

HRID 1971833 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[S:10]([Cl:14])(=O)(=[O:12])[OH:11]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([S:10]([Cl:14])(=[O:12])=[O:11])[CH:3]=1

Participants

3

Reactant 2

HCID 99874-FluoroanisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 27834095-Fluoro-2-methoxybenzene-1-sulfonyl chlorideYield 84.6%

Procedure

1-fluoro-4-methoxybenzene (10.0 g, 0.079 mol) was added dropwise to sulfurochloridic acid (31.4 ml, 0.474 mol) at 0° C., The mixture was stirred at room temperature for about 6 h, after which it was added dropwise into ice water. The mixture was extracted with CH2Cl2 three times. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo to give the title product (15.0 g, 84.6% yield).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 three times
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5683afa77cf4f7d9876a1220fe064da
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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