tert-Butyldimethylsilyl chloride → HCID 67060801, compound

HRID 1186078Notes

Reaction equation

HRID 1186078 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:7]=1.C(N(C(C)C)CC)(C)C.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:7]=1)[NH:8][CH2:9][CH2:10][CH2:11][O:12][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 65341400HCID 65341400, compound

Product 1

HCID 67060801HCID 67060801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((5-bromo-2-nitrophenyl)amino)propan-1-ol (6.73 g, 24.45 mmol) was dissolved in dry dichloromethane (50 mL), and diisopropylethyl amine (6.41 mL, 36.7 mmol) and tert-butyldimethylsilyl chloride (4.42 g, 29.3 mmol) were added. This mixture was stirred at room temperature for 3 h. The organic layer was washed with water, then saturated aqueous ammonium chloride, and then brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to give crude 5-bromo-N-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-nitroaniline as an orange oil which was used without further purification.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-600cfc53f5244ce6aeda40a27654c5ce
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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