Water → HCID 11484632, compound

HRID 266684Notes

Reaction equation

HRID 266684 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([N+:10]([O-])=O)[CH:7]=[CH:8][CH:9]=1.O>[Zn].CCOCC>[Br:3][C:4]1[CH:5]=[C:6]([NH:10][NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Br:3])[CH:5]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11457Benzene, 1-bromo-3-nitro-HCID 14798Sodium Hydroxide2×

Product 1

HCID 11484632HCID 11484632, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 50% NaOH (3.6 mL, 45 mM) was added 3-bromonitrobenzene (15 g, 74 mM) and the resulting solution was heated to 60° C. Zinc dust (11 g, 170 mM) was added in portions in such a manner as to keep the reaction temperature below 80° C. After the addition was complete, 20% NaOH (22 mL, 113 mM) was added followed by water (37 mL). An additional portion of zinc dust (14 g, 220 mM) was then added in one portion. The resulting mixture was heated at 70° C. for 1 hour, cooled to room temperature, and poured into ether (200 mL). The liquid was decanted away from the solids and the solids were resuspended in ether and this procedure was repeated an additional three times. The organic layers were combined, dried over Na2SO4, and concentrated. Purification by flash column chromatography afforded the titled compound as a white solid (10.1 g, 79%). NMR (CDCl3): 6.99 (m, 6H), 6.76 (dd, J1 =1 Hz, J2 =8 Hz), 5.66 (br s, 2H). MS(CI): 341/343(M+1).

Workup

  1. customthe reaction temperature below 80° C
  2. additionAfter the addition
  3. temperatureThe resulting mixture was heated at 70° C. for 1 hour
  4. temperaturecooled to room temperature
  5. customThe liquid was decanted away from the solids
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-42bfdf8cb9be44e2a964cbd58d891863
Source dataset
uspto-grants-1997_07
Patent number
US05652239

Reaction notes

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