Chlorine → HCID 58934979, compound

HRID 854974Notes

Reaction equation

HRID 854974 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([CH:8]=[C:9]([C:18]([OH:20])=[O:19])[CH:10]([C:14]([F:17])([F:16])[F:15])[O:11]3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[Cl:21]Cl>CC(O)=O.[Zn]>[Cl:21][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:4]=1[CH:1]1[CH2:2][CH2:3]1)[O:11][CH:10]([C:14]([F:15])([F:17])[F:16])[C:9]([C:18]([OH:20])=[O:19])=[CH:8]2

Participants

5

Reactant 2

HCID 24526ChlorineHCID 58934812HCID 58934812, compound

Product 1

HCID 58934979HCID 58934979, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a solution of the product of Example 146 Step 2 (0.28 g, 1.0 mmol) in 5 mL HOAc was added Cl2 in HOAc (3.0 mL, −1.5 mmol). After 0.75 h, the reaction was treated with Zn dust for 1.5 h. The reaction mixture was decanted from the Zn and concentrated under vacuum. The resulting residue was triturated with H2O, filtered, and washed with H2O. The yield of 6-chloro-7-cyclopropyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid was 0.26 g (82%) after drying overnight in a vacuum oven at 50° C.

Workup

  1. customThe reaction mixture was decanted from the Zn
  2. concentrationconcentrated under vacuum
  3. customThe resulting residue was triturated with H2O
  4. filtrationfiltered
  5. washwashed with H2O
  6. customafter drying overnight in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-1feff88901d94a039a789bd3753e0428
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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