(4-Fluorophenyl)-2-thiazolylmethanone → HCID 57428843, compound

HRID 2267394Notes

Reaction equation

HRID 2267394 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:15][Mg]Br>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)([OH:9])[CH3:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2758956(4-Fluorophenyl)-2-thiazolylmethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 57428843HCID 57428843, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (4-fluorophenyl)(thiazol-2-yl)methanone (1.05 g, 5.07 mmol) in diethyl ether (50 mL) and was cooled to 0° C., treated with methylmagnesium bromide (1.85 mL, 3.0 M in Et2O, 5.57 mmol) and stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride solution, extracted with diethyl ether (2×30 mL), washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as an oily brown residue (1.052 g, 93% yield). MS (M+H)+ 224.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with diethyl ether (2×30 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d240bcba446c4c0da53c31855b421700
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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