Benzyl Bromide → 4-Benzyloxy-benzenesulfonic acid 4-amino-3-nitrophenyl ester

HRID 1823777Notes

Reaction equation

HRID 1823777 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:10][C:9]=1[N+:25]([O-:27])=[O:26].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O.CN(C)C=O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:22][CH:23]=2)(=[O:16])=[O:17])=[CH:10][C:9]=1[N+:25]([O-:27])=[O:26]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86596077HCID 86596077, compound

Product 1

HCID 865960764-Benzyloxy-benzenesulfonic acid 4-amino-3-nitrophenyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of cesium carbonate (156 mg) in water (0.3 ml) was added to a solution of 4-hydroxy-benzenesulfonic acid 4-amino-3-nitro-phenyl ester (150 mg) and benzyl bromide (58 μl) in dimethylformamide (3 ml). The reaction mixture was heated at 80° C. for 3 hours then allowed to cool to ambient temperature, poured into water (25 ml) and extracted three times with ethyl acetate (30 ml). The combined extracts were dried over magnesium sulfate then evaporated to give 189 mg of crude 4-benzyloxy-benzenesulfonic acid 4-amino-3-nitrophenyl ester.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted three times with ethyl acetate (30 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthen evaporated

Sources & evidence

ORD record
ord-a7bed9eaf87e4e62adec3d48e60a22ab
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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