Methyl 2-Bromo-5-nitrobenzoate → Methyl (3'-chloro-2'-methoxy4-nitro-2-biphenylcarboxylate)

HRID 1938473Notes

Reaction equation

HRID 1938473 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[C:18](F)[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])=[CH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:4].BrC1C=CC([N+]([O-])=O)=CC=1C(OC)=O.[Cl:37]C1C=CC(OC)=C(B(O)O)C=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:37])[C:15]=2[O:21][CH3:22])=[CH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 10733357Methyl5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate

Product 1

HCID 54298406Methyl (3'-chloro-2'-methoxy4-nitro-2-biphenylcarboxylate)Yield 35%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

This compound was prepared in a manner similar to that of methyl(5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate) (EXAMPLE 107) from methyl 2-bromo-5-nitrobenzoate (0.58 g, 2.2 mmol), (PPh3)4 Pd (77 mg, 0.066 mmol), and 5-chloro-2-methoxyphenylboronic acid (0.54 g, 2.9 mmol) to afford 245 mg (35%) of methyl(3'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate) as a clear oil. Data for methyl(3'-chloro-2'-methoxy-4-nitro-2-biphenylcarboxylate): 1H NMR (400 MHz, CDCl3) 8.79 (d, J=2.4, 1H), 8.40 (dd, J=8.4, 2.4, 1H), 7.57 (d, J=8.5, 1H), 7.45 (m, 1H), 7.15 (m, 2H), 3.75 (s, 3H), 3.47 (s, 3H).

Sources & evidence

ORD record
ord-4994e03167e741e3931ff05b02975de4
Source dataset
uspto-grants-1997_12
Patent number
US05693647

Reaction notes

Loading…