Chlorosulfonic acid → 2-Fluoro-5-(2-oxo-propyl)-benzenesulfonyl chloride

HRID 1092956Notes

Reaction equation

HRID 1092956 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1>>[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14](=[O:16])[CH3:15])=[CH:11][C:12]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 521187(4-Fluorophenyl)acetone

Product 1

HCID 858617322-Fluoro-5-(2-oxo-propyl)-benzenesulfonyl chloride

Procedure

To chlorosulfonic acid (25 ml, excess) cooled at −10° C. is added dropwise 4-fluorophenyl acetone (1.0 g, 6.57 mmol). The temperature is kept below 0° C. throughout the addition. The reaction mixture is then left to warm up to room temperature overnight. The reaction mixture is poured carefully onto ice (1500 ml). Once ice is melted, the aqueous layer is extracted with DCM (3×250 ml). The combined organic layers are dried over MgSO4, filtered and concentrated to afford the titled compound as an off-white solid.

Workup

  1. additionThe temperature is kept below 0° C. throughout the addition
  2. waitThe reaction mixture is then left
  3. additionThe reaction mixture is poured carefully onto ice (1500 ml)
  4. extractionthe aqueous layer is extracted with DCM (3×250 ml)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f05ce92f5a73407f9869c4f0dd8e12b3
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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