Hydrochloric Acid → HCID 68193220, compound

HRID 1626822Notes

Reaction equation

HRID 1626822 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:21])([F:20])C(OCC)=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:22][Mg]I.C([O:27][CH2:28][CH3:29])C.Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:20])([F:21])[C:28]([CH3:29])([OH:27])[CH3:22])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68196377HCID 68196377, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 68193220HCID 68193220, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (4′-bromobiphenyl-4-yl)(difluoro)acetate (0.10 g, 0.28 mmol) obtained in Example 30-(1) was dissolved in tetrahydrofuran (20 mL), and a solution of methylmagnesium iodide in diethyl ether (3.0 M, 1.0 mL, 3.0 mmol) was added under a nitrogen atmosphere at room temperature, followed by stirring at the same temperature for 5 hours. Hydrochloric acid (1 M) was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the extract was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.35 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.063 g, 0.18 mmol) as a yellow oil (yield 62%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialsubsequently the extract was dried over anhydrous sodium sulfate
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.35 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bacd91d309ce4ce6bce9511d69a701f3
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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