(4-Chlorophenyl)(2-fluorophenyl)methanone → HCID 55026142, compound

HRID 449141Notes

Reaction equation

HRID 449141 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:9])=[CH:4][CH:3]=1.[CH3:17][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])([OH:9])[CH3:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 43160405(4-Chlorophenyl)(2-fluorophenyl)methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 55026142HCID 55026142, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of (4-chlorophenyl)-(2-fluorophenyl)-methanone (200 mg, 0.717 mmol) in THF (6 mL) was added 1.4 M of methylmagnesium bromide in THF (1.8 mL, 2.5 mmol) slowly at −78° C. The reaction was stirred at −78° C. for 4 h. The reaction was quenched with sat. aq. NaHCO3 at −78° C. The crude material was extracted with DCM and concentrated in vacuo to afford the title compound as a colorless oil which was used for next step without further purification.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3 at −78° C
  2. extractionThe crude material was extracted with DCM
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-051154c43c47400aafffdd000da65369
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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