Water → N-(2-(benzyloxy)-4-bromo-6-nitrophenyl)acetamide

HRID 2239286Notes

Reaction equation

HRID 2239286 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([NH2:6])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21].O>C(O)(=O)C.S(=O)(=O)(O)O>[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([NH:6][C:20](=[O:22])[CH3:21])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 672209592-(Benzyloxy)-4-bromo-6-nitroaniline

Product 1

HCID 67220372N-(2-(benzyloxy)-4-bromo-6-nitrophenyl)acetamideYield 83%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-2-nitro-6-[(phenylmethyl)oxy]aniline (33.0 g, 102 mmol, WO 2004054984) and acetic anhydride (14.5 mL, 153 mmol) in acetic acid (90 mL) was added concentrated sulfuric acid (2 drops) at 70° C. The mixture was stirred at 70° C. for 20 minutes. After cooling to room temperature, water (800 mL) was added, and the formed precipitate was collected by filtration, and washed with diisopropyl ether to give the title compound as a brown solid (30.9 g, 83%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe formed precipitate was collected by filtration
  3. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-94ea15b4df0c48c198ca4ccc58893ce1
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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