Triethylamine → 2-[(Tert-butyldimethylsilyl)oxy]-4-nitroaniline

HRID 1955822Notes

Reaction equation

HRID 1955822 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].Cl[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(CC)CC)C>ClCCl>[Si:13]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH2:1])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 154857102-[(Tert-butyldimethylsilyl)oxy]-4-nitroanilineYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 2-amino-5-nitrophenol (5.62 g, 36.5 mmol) and chloro-t-butyldimethylsilane (5.00 g, 33.2 mmol) in dry dichloromethane (66 mL) was added triethylamine (5.55 mL, 39.8 mmol) at 25° C. The reaction mixture was stirred at ambient temperature for 4 hours and partitioned between diethyl ether (200 mL) and saturated ammonium chloride. The aqueous layer was separated and the ether layer washed (saturated ammonium chloride, 1×; water, 1×; brine, 1×), dried (MgSO4), filtered, and evaporated in vacuo. Crystallization from ethyl acetate/hexanes gave 7.5 g (84%) of O-t-butyldimethylsilyl-2-amino-5-nitrophenol.

Workup

  1. custompartitioned between diethyl ether (200 mL) and saturated ammonium chloride
  2. customThe aqueous layer was separated
  3. washthe ether layer washed (saturated ammonium chloride, 1×; water, 1×; brine, 1×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customCrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2576bc4d8518477f964abe22fa1fc887
Source dataset
uspto-grants-1998_07
Patent number
US05776984

Reaction notes

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