Dichloromethane → (1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl ester

HRID 1681378Notes

Reaction equation

HRID 1681378 reaction equation
NC[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.F[C:14]1[CH:19]=[CH:18][C:17](F)=[CH:16][C:15]=1[N+]([O-])=O.[C:24](=O)([O-])[O-].[K+].[K+].ClCCl>CN(C=O)C>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([C:5]2[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=[CH:3][CH:4]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 677672,5-DifluoronitrobenzeneHCID 571728Methyl 4-(aminomethyl)benzoate

Product 1

HCID 1393873(1,1'-Biphenyl)-2-carboxylic acid, 4'-methyl-, methyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-aminomethylbenzoate (0.50 g) (obtained by acid-catalysed esterification of 4-aminomethylbenzoic acid), 2,5 difluoronitrobenzene (0.40 g) and potassium carbonate (0.35 g) in DMF (5 ml) was heated at 100° for 5 hours. The mixture was cooled, dichloromethane (20 ml) was added and insoluble material was removed by filtration. The solvent was evaporated and the residue recrystallised from methanol/ethyl acetate to give methyl 4-N-(4-fluoro-2-nitrophenyl)aminomethylbenzoate (B) (0.54 g) as orange needles, m.p. 144°-146° C.; NMR (CDCl3): 3.92(s, 3H), 4.61(d, 2H), 6.70(dd, 1H), 7.17(ddd, 1H), 7.62(d, 2H), 7.93(dd, 1H), 8.04(d, 2H), 8.36(br s, 1H); microanalysis found: C, 59.0; H, 4.1; N, 9.0; C15H13FN2O4 requires: C, 59.2; H, 4.3; N, 9.2%.

Workup

  1. temperaturewas heated at 100° for 5 hours
  2. temperatureThe mixture was cooled
  3. custominsoluble material was removed by filtration
  4. customThe solvent was evaporated
  5. customthe residue recrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-eba29f6f20a04970a47dc75f2cfb6556
Source dataset
uspto-grants-1992_12
Patent number
US05171748

Reaction notes

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