Chlorine → HCID 69518201, compound

HRID 854964Notes

Reaction equation

HRID 854964 reaction equation
[F:1][C:2]([F:22])([F:21])[CH:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]2[CH:9]=[C:8]3[O:18][CH2:19][O:20][C:7]3=[CH:6][C:5]=2[O:4]1.[Cl:23]Cl>C(O)(C(F)(F)F)=O.[Zn]>[Cl:23][C:9]1[C:10]2[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]([C:2]([F:21])([F:1])[F:22])[O:4][C:5]=2[CH:6]=[C:7]2[O:20][CH2:19][O:18][C:8]=12

Participants

5

Reactant 2

HCID 24526Chlorine2×HCID 69518071HCID 69518071, compound

Product 1

HCID 69518201HCID 69518201, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6422Trifluoroacetic acidSolvent2×

Procedure

To a solution of ethyl 6-(trifluoromethyl)-6H-[1,3]dioxolo[4,5-g]chromene-7-carboxylate (500 mg, 1.58 mmoles) in 6 mL of TFA was added a solution of Cl2 6 mL, 0.28M) in TFA. After 30 min, another 6 mL of Cl2 solution was added and stirring continued. Zn dust (1.00 g, 15.3 mg-atm) was added, and stirred overnight. After concentration, the residue was chromatographed over silica gel using 20% EtOAc—hexane as eluent to give the title compound, 460 mg, as a yellow solid.

Workup

  1. stirringstirred overnight
  2. concentrationAfter concentration
  3. customthe residue was chromatographed over silica gel using 20% EtOAc—hexane as eluent

Sources & evidence

ORD record
ord-0366bb42e5e64001a766c1cfe8b01889
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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