Toluene → Ethyl 3-bromo-5-nitrobenzoate

HRID 269558

Reaction equation

HRID 269558 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([OH:11])=[O:10].[C:18]1(C)C=CC=C[CH:19]=1>>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([O:11][CH2:18][CH3:19])=[O:10]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 2393363-Bromo-5-nitrobenzoic acid

Product 1

HCID 26966738Ethyl 3-bromo-5-nitrobenzoateYield 79%

Procedure

Thionyl chloride (15.7 g, 120 mmol) was added to a solution of 3-bromo-5-nitrobenzoic acid in toluene (100 ml). The mixture was refluxed for 6 hours. The solvent was evaporated and the residue dissolved in dry tetrahydrofuran (50 ml), ethanol (10 ml) was added and the mixture stirred at room temperature for 30 mins. The solvent was evaporated and the residue chromatographed in dichloromethane to give the title compound as an off-white solid (13 g, 79%)

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in dry tetrahydrofuran (50 ml)
  4. additionethanol (10 ml) was added
  5. customThe solvent was evaporated
  6. customthe residue chromatographed in dichloromethane

Sources & evidence

ORD record
ord-84821d5048f34e8ca13f99747fb0b754
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Linked notes

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