Chlorine → HCID 69517714, compound

HRID 854951Notes

Reaction equation

HRID 854951 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]([C:13]([F:16])([F:15])[F:14])[O:9]2)=[CH:4][CH:3]=1.[Cl:22]Cl>CC(O)=O>[Cl:22][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:12])[C:2]=1[CH3:1])[O:9][CH:8]([C:13]([F:16])([F:14])[F:15])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6]2

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 69516565HCID 69516565, compound

Product 1

HCID 69517714HCID 69517714, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 7,8-dimethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylat (4.0 g, 13.3 mmol) in 75 mL HOAc was added Cl2 until the solvent was saturated as indicated by the greenish chlorine cloud above the solvent. After 2 h, the reaction was flushed with N2 and subsequently treated with excess Zn dust for 1.5 h. The reaction mixture was decanted from the Zn and concentrated under vacuum. The resulting residue was dissolved in 300 mL of EtOAc and washed with 100 mL 1 M KHSO4 and 100 mL brine. The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The yield of ethyl 6-chloro-7,8-dimethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate was 5.2 g.

Workup

  1. customthe reaction was flushed with N2
  2. additionsubsequently treated with excess Zn dust for 1.5 h
  3. customThe reaction mixture was decanted from the Zn
  4. concentrationconcentrated under vacuum
  5. dissolutionThe resulting residue was dissolved in 300 mL of EtOAc
  6. washwashed with 100 mL 1 M KHSO4 and 100 mL brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7fd4eff211014cc9acdde63902cd40bd
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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