Methyl 2-Bromo-5-nitrobenzoate → Methyl-5'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate

HRID 1604781Notes

Reaction equation

HRID 1604781 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:15][C:16]1[CH:21]=[C:20](C2C=CC=CC=2)[C:19]([O:31][CH3:32])(C([O-])=O)[CH2:18][C:17]=1[N+]([O-])=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][O:6][C:4]([C:3]1[C:2]([C:20]2[CH:21]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]=2[O:31][CH3:32])=[CH:11][CH:10]=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 867548835-Chloro-2-methoxy-4-nitro-2-biphenylcarboxylate

Product 1

HCID 10829633Methyl-5'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

This compound was prepared in a manner similar to that of methyl-(5'-fluoro-2'-fluoro-2'-methoxy-4-nitro-2-biphenyl)carboxylate (EXAMPLE 107) from methyl 2-bromo-5-nitrobenzoate (1.25 g, 4.8 mmol, 1.0 equivuiv), tetrakis(triphenylphosphine) palladium (Aldrich: 0.16 g, 0.14 mmol, 2.9 mol%), and 5-chloro-2-methoxy-4-nitro-2-biphenylcarboxylate as a to afford 0.85 g (55%) of methyl-5'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate as a yellow-orange solid. Data for methyl-5'-2'-methoxy-4-nitro-2-biphenylcarboxylate: 1H NMR (400 MHz, CDCl3): 8.73 (d, J=2.4, 1 H); 8.38 (dd, J=8.5, 2.5, 1 H); 7.49 (d, J=8.5, 1 H); 7.36 (dd, J=8.7, 2.5, 1 H); 7.23 (d, J=2.5, 1 H); 6.85 (d, J=8.7, 1 H); 3.76 (s, 3 H); 3.70 (s, 3 H).

Sources & evidence

ORD record
ord-877c70e7378e45c7bb73adc8db632b85
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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