1,2-Dibromoethane → HCID 68810143, compound

HRID 2249368Notes

Reaction equation

HRID 2249368 reaction equation
[C:1]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C([Li])CCC.C(Br)C[Br:24]>O1CCCC1>[C:1]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=1[Br:24])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 22327316HCID 22327316, compoundHCID 178418339Butyllithium

Product 1

HCID 68810143HCID 68810143, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To solution of N-pivaloyl-4-chloro-3-methoxyaniline (5.0 g, 21 mmol) in tetrahydrofuran (60 mL) at −60° C. was added n-butyl lithium (2.5M, 44 mmol). The solution was allowed to warm to 0° C. and stir for 3 hours. Ethylene dibromide (9.9 g, 53 mmol) was added and the solution stirred for 18 hours before being quenched with with ammonium chloride (saturated solution, 20 mL) and extracted with ethyl ether (2×50 mL). The combined extracts were washed with brine, dried (sodium sulfate) and concentrated. The residure was purified by chromatography (10% ethyl acetate/hexanes) to give N-pivaloyl-2-bromo-4-chloro-3-methoxyaniline (3.7 g, 1.2 mmol): LC/MS (m/z=320).

Workup

  1. stirringthe solution stirred for 18 hours
  2. custombefore being quenched with with ammonium chloride (saturated solution, 20 mL)
  3. extractionextracted with ethyl ether (2×50 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe residure was purified by chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5cf0adc3df5f432885f3368a8c3aa757
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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