Ammonium Chloride → 1400701-89-4

HRID 878773Notes

Reaction equation

HRID 878773 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([Cl:14])[CH:3]=1.[CH:15]1([Mg]Br)[CH2:17][CH2:16]1.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([CH:15]2[CH2:17][CH2:16]2)=[O:7])=[C:4]([Cl:14])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 598430764-bromo-2-chloro-N-methoxy-N-methylbenzamideHCID 178418630HCID 178418630, compound

Product 1

HCID 682899851400701-89-4Yield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (synthesized by the method of Bioorganic & Medicinal Chemistry Letters 2003, 13, 3983, 5.90 g, 21.0 mmol) in tetrahydrofuran (180 mL) was added dropwise a solution of 0.7 mol/L cyclopropylmagnesium bromide in tetrahydrofuran (65.0 mL, 45.5 mmol) at 0° C. The mixture was stirred at the same temperature for 4 hours, and then to the reaction solution was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→93:7) to give (4-bromo-2-chlorophenyl)(cyclopropyl)methanone (3.75 g, 68%) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→93:7)

Sources & evidence

ORD record
ord-b25036fd85b1441b9fe75fdde187b42c
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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