Methanol → Methyl 2-(4-fluorophenyl)-4-nitrobenzoate

HRID 2187611Notes

Reaction equation

HRID 2187611 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1.CO>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:15]=2[C:16]([O:18][CH3:1])=[O:17])=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 184760234'-Fluoro-5-nitro[1,1'-biphenyl]-2-carboxylic acid

Product 1

HCID 18476040Methyl 2-(4-fluorophenyl)-4-nitrobenzoateYield 95.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (9.35 g; 0.074 mol) was added to a solution of 2-(4-fluorophenyl)-4-nitrobenzoic acid (17.5 g; 0.067 mol) in methylene chloride (150 ml). After addition of DMF (3 drops), the mixture was stirred at ambient temperature for 2 hours. After evaporation to dryness the residue was redissolved in methylene chloride (100 ml); methanol (50 ml) and DMAP (8.2 g; 0.067 mol) was added at 0° C. After stirring at ambient temperature for 2 hours, the mixture was evaporated to dryness. The residue was taken up in methylene chloride washed with a 2N HCl, saturated aqueous sodium bicarbonate and evaporated to give methyl 2-(4-fluorophenyl)-4-nitrobenzoate (17.6 g; 95%).

Workup

  1. customAfter evaporation to dryness the residue
  2. dissolutionwas redissolved in methylene chloride (100 ml)
  3. stirringAfter stirring at ambient temperature for 2 hours
  4. customthe mixture was evaporated to dryness
  5. washwashed with a 2N HCl, saturated aqueous sodium bicarbonate
  6. customevaporated

Sources & evidence

ORD record
ord-a057400548ba4b68817649dee745204d
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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