Ammonium Chloride → (4-(Allyloxy)-5-bromo-2-chlorophenyl)(4-ethylphenyl)methanone

HRID 576314Notes

Reaction equation

HRID 576314 reaction equation
[CH2:1]([O:4][C:5]1[C:16]([Br:17])=[CH:15][C:8]([C:9](N(OC)C)=[O:10])=[C:7]([Cl:18])[CH:6]=1)[CH:2]=[CH2:3].[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1)[CH3:20].[NH4+].[Cl-]>C1COCC1>[CH2:1]([O:4][C:5]1[C:16]([Br:17])=[CH:15][C:8]([C:9]([C:24]2[CH:25]=[CH:26][C:21]([CH2:19][CH3:20])=[CH:22][CH:23]=2)=[O:10])=[C:7]([Cl:18])[CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 867140214-(Allyloxy)-5-bromo-2-chloro-N-methoxy-N-methylbenzamideHCID 178436501HCID 178436501, compound

Product 1

HCID 86714031(4-(Allyloxy)-5-bromo-2-chlorophenyl)(4-ethylphenyl)methanoneYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of Weinreb amide 22 (4.5 g, 13.4 mmol) in THF (100 mL) was added 4-ethylphenylmagnesium bromide (0.5M in THF, 50.8 mL, 26.9 mmol) at 0° C. The reaction mixture was warmed up to r.t. slowly and stirred at r.t. for 15 hours. To the reaction mixture was added aqueous saturated NH4Cl solution (100 mL). The mixture was extracted with EtOAc (100 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with hexane (100 mL) and stirred at r.t. for 30 min. The solid was precipitated, filtered, washed with hexane (50 mL) and dried under high vacuum to obtain the title product (4.30 g, 73%).

Workup

  1. extractionThe mixture was extracted with EtOAc (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with hexane (100 mL)
  6. stirringstirred at r.t. for 30 min
  7. customThe solid was precipitated
  8. filtrationfiltered
  9. washwashed with hexane (50 mL)
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-17526153305848e381264fc0d39a2ce7
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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