4-Bromo-1,2-dichlorobenzene → Ammonia

HRID 1986045Notes

Reaction equation

HRID 1986045 reaction equation
[NH2:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.CC(C)([O-])C.[K+].[Cl:18][C:19]1[CH:20]=[C:21](Br)[CH:22]=[CH:23][C:24]=1[Cl:25].O1CCOCC1>O>[NH3:1].[ClH:18].[Cl:18][C:19]1[CH:20]=[C:21]([NH:1][CH:2]2[CH2:3][C:4]([CH3:11])([CH3:10])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7]2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

7

Reactant 4

HCID 290134-Bromo-1,2-dichlorobenzeneHCID 312751,4-DioxaneHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 23665647Potassium tert-butoxide

Product 2

HCID 222AmmoniaHCID 67046446HCID 67046446, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-amino-2,2,6,6-tetramethylpiperidine (3.4 ml, 20 mmol), potassium tert-butoxide (4.5 g, 40 mmol), 3,4-dichlorobromobenzene (4.97 g, 22 mmol), palladacycle (100 mg, 0.11 mmol) and dioxane (100 ml) was stirred at reflux for 2 h. Water (100 ml) was added and the mixture was extracted with diethyl ether (2×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 5.56 g, (82%). Hydrochloric acid in ether (6.5 ml, 3.1 M) was added and the hydrochloric acid salt was precipitated and stirred for 10 min, followed by filtration. Mp >300° C.

Workup

  1. temperatureat reflux for 2 h
  2. extractionthe mixture was extracted with diethyl ether (2×50 ml)

Sources & evidence

ORD record
ord-a7066928bae5487bb60b7de46b0548d0
Source dataset
uspto-grants-2009_06
Patent number
US07547788B2

Reaction notes

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