Bromide ion → HCID 22413567, compound

HRID 1721679Notes

Reaction equation

HRID 1721679 reaction equation
[Mg].II.[Br-].[S:5]1[CH:9]=[C:8]([CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)[N:7]=[CH:6]1.[NH4+].[Cl-]>C1COCC1.C1(CBr)CCCCC1>[CH:15]1([CH2:16][C:16]([C:15]2[CH:18]=[CH:19][C:12]([O:11][CH2:10][C:8]3[N:7]=[CH:6][S:5][CH:9]=3)=[CH:13][CH:14]=2)=[O:17])[CH2:18][CH2:19][CH2:12][CH2:13][CH2:14]1.[CH:15]1([CH2:16][CH:16]([C:15]2[CH:18]=[CH:19][C:12]([O:11][CH2:10][C:8]3[N:7]=[CH:6][S:5][CH:9]=3)=[CH:13][CH:14]=2)[OH:17])[CH2:18][CH2:19][CH2:12][CH2:13][CH2:14]1

Participants

9

Reactant 5

HCID 259Bromide ionHCID 807IodineHCID 25517Ammonium ChlorideHCID 8209774-(1,3-thiazol-4-ylmethoxy)benzaldehydeHCID 5462224Magnesium

Product 2

HCID 22413567HCID 22413567, compoundHCID 67694929HCID 67694929, compound

Reagents, catalysts & solvents 2

HCID 137636Cyclohexane, (bromomethyl)-CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A suspension of magnesium turnings (840 mg, 35 g-atom) in THF (25 mL) was activated with iodine crystalls. A few drops of cyclohexylmethyl bromide were added, and the mixture was warmed until the exothermic Grignard reaction commenced. The remaining bromide (4.9 mL; 35 mmol) was added dropowise at a rate sufficient to maintain a gentle reflux. The mixture was refluxed for an additional 30 minutes, cooled to -78° C., and then slowly cannulated to a cold Solution of 4-(4-thiazolylmethoxy)benzaldehyde (7.6 g, 35 mmol), prepared as in step 1, in THF (75 mL), and the resulting solution was allow to stand at ambient temperature for 12 hours. Saturated aqueous NH4Cl (50 mL) was added and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified on a silica gel column eluting with 7:3 hexane-ethyl acetate to provide 900 mg of cyclohexylmethyl-(4-(4-thiazolylmethoxy)phenyl) ketone and 5.4 g of 2-cyclohexyl-1-(4-(4-thiazolylmethoxy)phenyl)ethan-1-ol.

Workup

  1. temperaturethe mixture was warmed until the exothermic Grignard reaction
  2. temperatureto maintain a gentle reflux
  3. temperatureThe mixture was refluxed for an additional 30 minutes
  4. extractionthe mixture was extracted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on a silica gel column
  9. washeluting with 7:3 hexane-ethyl acetate

Sources & evidence

ORD record
ord-10a000fa2ee04893a300ebec065bf2fe
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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