1,2-Dibromoethane → HCID 68810143, compound

HRID 1782598Notes

Reaction equation

HRID 1782598 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 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 residue 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 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 residue was purified by chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f99afb92009b46ea86278f95b19f5328
Source dataset
uspto-grants-2009_03
Patent number
US07498468B2

Reaction notes

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