Water → HCID 86749496, compound

HRID 2255891Notes

Reaction equation

HRID 2255891 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[C:16]([F:18])[C:15]([C:19]([F:22])([F:21])[F:20])=[C:14]([Cl:23])[CH:13]=2)=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH-].[NH4+:25].O>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[C:16]([F:18])[C:15]([C:19]([F:22])([F:21])[F:20])=[C:14]([Cl:23])[CH:13]=2)=[CH:7][C:3]=1[C:4]([NH2:25])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 86749497HCID 86749497, compound

Product 1

HCID 86749496HCID 86749496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-bromo-5-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]benzoyl chloride (16 g, 0.036 mol) in methylene chloride is cooled to 0° C., treated dropwise with 9.2 mL of a 30% ammonium hydroxide solution (0.071 mol), stirred at 0° C. for 30 minutes, stirred at room temperature overnight and poured into water. The aqueous mixture is extracted with methylene chloride. The organic extracts are combined, washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a white solid, mp 115°-116° C.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionThe aqueous mixture is extracted with methylene chloride
  3. washwashed sequentially with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b91aad5d1fe24587ad34f422d3680d8f
Source dataset
uspto-grants-1997_08
Patent number
US05654256

Reaction notes

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