Chlorosulfonic acid → HCID 86713311, compound

HRID 927970Notes

Reaction equation

HRID 927970 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[Cl:13][S:14]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 2734108Methyl 3-fluorophenylacetate

Product 1

HCID 86713311HCID 86713311, compound

Procedure

Methyl (3-fluorophenyl)acetate (1.51 g) was added dropwise to chlorosulphonic acid (7 mL) with stirring and ice cooling. The cooling bath was removed and the mixture was allowed to stand at room temperature for 16 hours before being carefully added to a mixture of ice and ethyl acetate. The organic layer was separated, washed with water, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give methyl (2-chlorosulfonyl-5-fluorophenyl)acetate (1.42 g) as a white solid.

Workup

  1. customThe cooling bath was removed
  2. additionbefore being carefully added to a mixture of ice and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

Sources & evidence

ORD record
ord-9c6cece0184b46298d44fb4f245e6fee
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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