Chlorine → HCID 69518339, compound

HRID 854903Notes

Reaction equation

HRID 854903 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:21][CH3:22])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2.[Cl:23]Cl>C(O)(=O)C>[Cl:23][C:5]1[C:4]([O:21][CH3:22])=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[CH:7]=[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]([C:12]([F:15])([F:14])[F:13])[O:10]2

Participants

4

Reactant 2

HCID 24526ChlorineHCID 69517224HCID 69517224, compound

Product 1

HCID 69518339HCID 69518339, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 8-chloro-6-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in U.S. Pat. No. 6,271,253 B1 Example 40 (2.32 g, 6.89 mmole) in glacial acetic acid (100 mL) was added Cl2 gas for 0.5 minutes. After standing for 20 min, the solvent was removed in vacuo and the remaining acetic acid was azeotroped with hexanes to give a crystalline solid containing a mixture of regioisomers. The crude product was purified by recrystallization from ethyl acetate-hexanes to give 189 mg (7.4% yield) of the product as colorless needles: EIHRMS m/z 369.9986 (M+, C14H11C2lF3O4, Calc'd 369.9986).

Workup

  1. customfor 0.5 minutes
  2. customthe solvent was removed in vacuo
  3. customthe remaining acetic acid was azeotroped with hexanes
  4. customto give a crystalline solid
  5. additioncontaining
  6. additiona mixture of regioisomers
  7. customThe crude product was purified by recrystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-55f4cd1fd8e24055a926684f06ee4df3
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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