Potassium Carbonate → HCID 66158876, compound

HRID 545628Notes

Reaction equation

HRID 545628 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9]Br.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.CCOC(C)=O>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][CH2:9][C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[Br:1])=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 118465052-Bromo-5-chlorobenzyl bromide

Product 1

HCID 66158876HCID 66158876, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-bromo-2-(bromomethyl)-4-chlorobenzene (1.70 g, 6 mmol) in ACN (10.0 mL) was added p-methoxybenzyl amine (0.91 g, 6.6 mmol) and potassium carbonate (2.08 g, 15.0 mmol) and the overall mixture was stirred at 80° C. overnight. After cooling, the reaction mixture was diluted with water (10 mL) and diluted with EtOAc (15 mL). The separated aqueous layer was extracted with EtOAc (10 mL×2) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a crude residue which was washed with hexanes to obtain the desired product N-(4-methoxybenzyl)(2-bromo-5-chlorophenyl)methanamine as a pale yellow solid. MS m/e 340 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. extractionThe separated aqueous layer was extracted with EtOAc (10 mL×2)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a crude residue which
  7. washwas washed with hexanes

Sources & evidence

ORD record
ord-67663f69c081419887f6a8cbe899579a
Source dataset
uspto-grants-2011_05
Patent number
US07935709B2

Reaction notes

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