Sulfuryl chloride → 2-Amino-3-chloro-5-(trifluoromethoxy)benzoic acid

HRID 1717458Notes

Reaction equation

HRID 1717458 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)([Cl:19])(=O)=O>CC(O)=O>[NH2:1][C:2]1[C:10]([Cl:19])=[CH:9][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 110853492-amino-5-(trifluoromethoxy)benzoic Acid

Product 1

HCID 219046192-Amino-3-chloro-5-(trifluoromethoxy)benzoic acidYield 107.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-amino-5-trifluoromethoxybenzoic acid (49.0 g, 0.22 mol; see step (ii) above) in HOAc (1200 mL) was slowly added sulfuryl chloride (41.8 g, 0.31 mol). Gas evolution was observed. The resulting heterogeneous mixture was stirred at room temperature for 1 h. Additional HOAc (300 mL) was added to aid stirring, followed by sulfuryl chloride in 5 mL portions until the starting material was consumed based on TLC analysis. The reaction was concentrated in vacuo to give solids that were flushed on a rotary evaporator with EtOAc (2×) followed by Et2O (1×) to remove the HOAc. The resulting solids were further dried to give the HCl salt of the crude sub-title compound (60.5 g, 94%), which was used in the next step without further purification.

Workup

  1. stirringstirring
  2. customwas consumed
  3. concentrationThe reaction was concentrated in vacuo
  4. customto give solids that
  5. customwere flushed on a rotary evaporator with EtOAc (2×)
  6. customto remove the HOAc
  7. customThe resulting solids were further dried

Sources & evidence

ORD record
ord-279001468c854fc0bdf3487386f5874f
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

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