Sodium Carbonate → HCID 66614114, compound

HRID 2276015Notes

Reaction equation

HRID 2276015 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[C:11]([CH3:16])=[N:12][N:13]([CH3:15])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:23]Br>ClCCl>[Br:23][C:14]1[N:13]([CH3:15])[N:12]=[C:11]([CH3:16])[C:10]=1[O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 66614262HCID 66614262, compound2×

Product 1

HCID 66614114HCID 66614114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-25 °C

Procedure

To a mixture of 4-(2-chloro-4-fluorophenyoxy)-1,3-dimethyl-1H-pyrazole (i.e. the product of Step B) (680 mg, 2.82 mmol) and sodium carbonate (389 mg, 3.67 mmol) in dichloromethane (12 mL) at −40° C. was added a solution of bromine (474 mg, 2.96 mmol) in dichloromethane (1 mL). After the addition was complete, the reaction mixture temperature was maintained at about −30 to −20° C. for 5 h. The reaction mixture was diluted with dichloromethane (50 mL) and washed with water (2×10 mL), aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a yellow solid (720 mg).

Workup

  1. additionAfter the addition
  2. washwashed with water (2×10 mL), aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96ba728b61fa4dd0ad508554bece703b
Source dataset
uspto-grants-2015_09
Patent number
US09131693B2

Reaction notes

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