Benzyl Bromide → 2-Benzyloxy-6-nitroaniline

HRID 1757466Notes

Reaction equation

HRID 1757466 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 37837412-Benzyloxy-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.16 g (40 mM) of 2-amino-3-nitrophenol, 60 ml of dimethylformamide and 6.62 g (48 mM) of dipotassium carbonate are introduced into a round-bottomed flask. 4.75 ml (40 mM) of benzyl bromide are then added dropwise and the reaction mixture is brought to 80° C. After havingbeen stirred under an inert atmosphere for 1.5 hours, the mixture is pouredinto ice-cold water and then extracted with 200 ml of ethyl acetate. The organic phase is separated by settling and, after washing with a saturatedsodium chloride solution, it is dried over magnesium sulphate and evaporated to dryness. The product is chromatographed on a silica column (eluent: 10% ethyl acetate and 90% hexane) to lead to 8.8 g (90%) of the expected compound in the form of an orangey oil.

Workup

  1. customis brought to 80° C
  2. extractionextracted with 200 ml of ethyl acetate
  3. customThe organic phase is separated
  4. washafter washing with a saturatedsodium chloride solution, it
  5. dry with materialis dried over magnesium sulphate
  6. customevaporated to dryness
  7. customThe product is chromatographed on a silica column (eluent: 10% ethyl acetate and 90% hexane)

Sources & evidence

ORD record
ord-2c1eb60540cf4bbaaebba4cc13b62d19
Source dataset
uspto-grants-1995_08
Patent number
US05446059

Reaction notes

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