Benzyl Bromide → N-(2-benzyloxy-4-nitro-phenyl)-acetamide

HRID 1354861Notes

Reaction equation

HRID 1354861 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCCCCC.CCOC(C)=O>CC(C)=O.C1COCC1>[CH2:21]([O:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamide2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 14166614N-(2-benzyloxy-4-nitro-phenyl)-acetamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Hydroxy-4-nitro-phenyl)-acetamide (417) (17 g, 86.7 mmol) was dissolved in a mixture of acetone (200 mL) and THF (200 mL). Potassium-carbonate (24 g, 173.4 mmol, 2 equiv.) was added as a dry powder and the solution turned deep red. Benzyl-bromide (16.3 g, 95.37 mmol, 1.1 equiv.) was added and the mixture stirred at room temperature for 20 h. TLC (Rf: 0.5 compared to Rf: 0.2–0.3 for compound 417 in 1:1 hexane/EtOAc) indicated complete alkylation at this point. The mixture was poured into ice water (˜1000 mL) and a precipitate formed while stirring for 20 min. The precipitate was collected by filtration under reduced pressure, washed with water (3×100 mL) and dried under high vacuum for 16 h to give the desired product (418) as a faintly yellow powder (13 g, 45.4 mmol, 51.7% yield). LC-MS was inconclusive. The product was used in the next step without further characterization

Workup

  1. customa precipitate formed
  2. stirringwhile stirring for 20 min
  3. filtrationThe precipitate was collected by filtration under reduced pressure
  4. washwashed with water (3×100 mL)
  5. customdried under high vacuum for 16 h

Sources & evidence

ORD record
ord-06deccc99e0f4711ab54015c80d91e4b
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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