Bromoacetyl bromide → Ammonium Hydroxide

HRID 2247221Notes

Reaction equation

HRID 2247221 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[NH2:14])([CH3:4])([CH3:3])[CH3:2].[Br:15][CH2:16][C:17](Br)=[O:18]>CN(C1C=CN=CC=1)C.C1COCC1>[NH4+:11].[OH-:12].[Br:15][CH2:16][C:17]([NH:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])=[O:18]

Participants

6

Reactant 2

HCID 61147Bromoacetyl bromideHCID 8261032-Tert-butyl-5-nitroaniline

Product 2

HCID 14923Ammonium HydroxideHCID 219613852-bromo-N-(2-tert-butyl-5-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-tert-Butyl-5-nitro-phenylamine (70 g, 359 mmol) and a catalytic amount of DMAP were dissolved in THF (1.5 L) under N2. TEA (109 g, 1077 mmol) was added and the solution was cooled to 0° C. Bromoacetyl bromide (207 g, 1023 mmol) was added and the reaction was gradually warmed to RT with stirring overnight. The reaction was partially concentrated under reduced pressure, treated with H2O and extracted with EtOAc (3×). The EtOAc extracts were washed with brine, combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure giving a black oil. This oil was eluted through a 38×7 cm column of silica gel with 95:5:0.5 CH2Cl2:MeOH:NH4OH(aq) eluant giving 2-bromo-N-(2-tert-butyl-5-nitro-phenyl)-acetamide as a brown solid.

Workup

  1. temperaturethe reaction was gradually warmed to RT
  2. concentrationThe reaction was partially concentrated under reduced pressure
  3. additiontreated with H2O
  4. extractionextracted with EtOAc (3×)
  5. washThe EtOAc extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customgiving a black oil
  10. washThis oil was eluted through a 38×7 cm column of silica gel with 95:5:0.5 CH2Cl2

Sources & evidence

ORD record
ord-9da4e7c6cce845be9f23f6954e2c5658
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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