Chlorine → HCID 69516738, compound

HRID 854865Notes

Reaction equation

HRID 854865 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[Cl:24]Cl>C(O)(=O)C.[Zn]>[Cl:24][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[O:4][CH2:1][CH2:2][CH3:3])[O:12][CH:11]([C:15]([F:18])([F:16])[F:17])[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:9]2

Participants

5

Reactant 2

HCID 24526Chlorine2×HCID 69519025HCID 69519025, compound

Product 1

HCID 69516738HCID 69516738, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

The ester from Step 1 (0.4 g, 1.2 mmole) in acetic acid (10 mL) was treated with Cl2 (gas) in HOAc solution (Pre-prepared 0.5 M) (7.3 ml, 3.6 mmole). The mixture was stirred for 3 hours. After Cl2 (gas) was blown away, Zn powder (3 eq) was added to the mixture and stirred for 30 min. The Zn salts were removed by filtration and the filtrate was evaporated to dryness. The residue was purified by flash chromatography with 10% ethyl acetate in hexane to give clear oil (0.33 g, 69%). This ester was of suitable purity to use without further purification.

Workup

  1. stirringstirred for 30 min
  2. customThe Zn salts were removed by filtration
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by flash chromatography with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d757393d6c0d435dbc7ea33cfb63a876
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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