Hexane → HCID 58046309, compound

HRID 2359285Notes

Reaction equation

HRID 2359285 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:5]([OH:7])=[O:6].[CH2:20]([Zn]CC)[CH3:21].CCCCCC>O1CCCC1>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[O:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8058HexaneHCID 58046322HCID 58046322, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 58046309HCID 58046309, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-4-(3,4-dichlorophenoxy)benzoic acid (Preparation 8, 240 mg, 0.663 mmol) was dissolved in anhydrous tetrahydrofuran (3 mL) and cooled to 0° C. Bis(tributylphosphine)palladium (0) (33.7 mg, 0.07 mmol) was added followed by the slow addition of a 1M solution of diethyl zinc in hexane (3.32 mL, 3.32 mmol). The reaction mixture was stirred overnight under an atmosphere of nitrogen. The reaction mixture was then quenched with a 1M aqueous solution of hydrogen chloride and extracted with ethyl acetate. The combined organic phase was concentrated in vacuo and the resulting residue then purified by reverse phase column chromatography (Trilution method) to afford the title compound as a white solid (75 mg, 36%).

Workup

  1. customThe reaction mixture was then quenched with a 1M aqueous solution of hydrogen chloride
  2. extractionextracted with ethyl acetate
  3. concentrationThe combined organic phase was concentrated in vacuo
  4. customthe resulting residue then purified by reverse phase column chromatography (Trilution method)

Sources & evidence

ORD record
ord-f597247b407443a783eb51d78b7a05bd
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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