Hydrochloric Acid → Methyl 4-(chlorosulfonyl)-2-fluorobenzoate

HRID 337215Notes

Reaction equation

HRID 337215 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([F:16])[CH:7]=1.[S:17](=[O:19])=[O:18].O.[ClH:21]>C(O)(=O)C.[Cu](Cl)Cl>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[CH:15][C:6]([S:17]([Cl:21])(=[O:19])=[O:18])=[CH:7][C:8]=1[F:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1119Sulfur DioxideHCID 21957875Methyl 4-amino-2-fluorobenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 57732146Methyl 4-(chlorosulfonyl)-2-fluorobenzoateYield 55%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×

Procedure

Sodium nitrite (0.54 g, 8.0 mmol) was added portion wise to a stirred solution of methyl 4-amino-2-fluorobenzoate (1.0 g, 6.0 mmol) in acetic acid (7 ml) and HCl (concentrated, 2.5 ml) while maintaining the temperature below 15° C. This solution was then added drop wise to a stirred solution of saturated sulfur dioxide, copper (II) chloride (0.25 g, 1.0 mmol) and water (0.5 ml) in acetic acid (5 ml) at 5° C. The reaction mixture was allowed to warm to room temperature and poured over ice water and stirred for a further 15 minutes. The resulting precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to give the title compound (1.5 g, 55% yield) as a pale brown solid which was used without further purification.

Workup

  1. temperaturewhile maintaining the temperature below 15° C
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-42501aa2725148e2ba4ee0714ce96384
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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