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

HRID 1990722Notes

Reaction equation

HRID 1990722 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-03d4a6f693804fbd9f93a9e0aa44e542
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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