Ammonium Chloride → HCID 68432882, compound

HRID 2426980Notes

Reaction equation

HRID 2426980 reaction equation
[Br-].[Mg+2].[Br-].[O:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[NH4+].[Cl-:19]>C1COCC1>[Cl:19][C:10]1[CH:17]=[CH:16][C:13]([CH:14]([C:13]2[CH:12]=[CH:11][C:10]([N:7]3[CH2:6][CH2:5][O:4][CH2:9][CH2:8]3)=[CH:17][CH:16]=2)[OH:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 82241Magnesium BromideHCID 2913494-Morpholinobenzaldehyde

Product 1

HCID 68432882HCID 68432882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-fluorophenyl)magnesium bromide (1M in THF, 10.6 ml. 10.6 mmol) at 0° C. was added a solution of 4-morpholinobenzaldehyde (1 g, 5.233 mmol) in THF (10 ml) dropwise. After being stirred at 0° C. for 10 minutes and room temperature for 4 hours, the reaction mixture was poured onto an iced aqueous NH4Cl. The solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated to give (4-chlorophenyl)(4-morpholinophenyl)methanol as a pinkish white solid (1.49 g, 99 yield). HPLC (Column: Shimadzu VP-0DS, C-18 Ballistic; 10-90% aq CH3OH/0.1% H3PO4, same for compounds hereafter unless noted) Rt: 2.117 min.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give

Sources & evidence

ORD record
ord-efc0f797a22f49908fee9603de6bda83
Source dataset
uspto-grants-2011_06
Patent number
US07968577B2

Reaction notes

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