Benzyl Bromide → 4-Benzyloxy-2-nitroaniline

HRID 883981Notes

Reaction equation

HRID 883981 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 2614974-Benzyloxy-2-nitroanilineYield 64%

Procedure

A solution containing 4-amino-3-nitro phenol (1.09 g, 7.07 mmole), benzylbromide (1.28 g, 7.5 mmole and cesium carbonate (2.43 g, 7.5 mmole) were stirred for 4 days at room temperature. After the reaction was complete, the reaction mixture was poured into ice water (500 ml), stirred 1 hour, and the resultant solid was filtered and dried under vacuum to provide the title compound (1.1 g, 64%).

Workup

  1. stirringstirred 1 hour
  2. filtrationthe resultant solid was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-6f0b778db4f740d4a01951420d984ee1
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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