Dimethylformamide → 5-Bromo-2-nitroaniline

HRID 1907709Notes

Reaction equation

HRID 1907709 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.C[N:18](C=O)C>COCCOC.[Cu]Cl>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([NH2:18])[CH:9]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 114661-Bromo-4-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 53147665-Bromo-2-nitroanilineYield 84%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of potassium tert-butoxide (21.92 g, 195 mmol) and copper (I) chloride (2.36 g, 23.8 mmol) in ethyleneglycol dimethylether (170 mL), stirred at 0° C. under nitrogen, a solution of 1-bromo-4-nitrobenzene (141, 8.69 g, 43.0 mmol) in DMF (45 mL) was added drop wise over 50 min. After complete addition the cooling bath was removed and the mixture was allowed to stir at room temperature for 4 h, diluted with DCM, washed with aqueous NH4Cl, dried over MgSO4, filtered and concentrated to give compound 142 (7.85 g, 84% yield).

Workup

  1. additionAfter complete addition the cooling bath
  2. customwas removed
  3. additiondiluted with DCM
  4. washwashed with aqueous NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-11cee16379b64e9bb66ec737842b4d24
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

Loading…