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

HRID 1604795Notes

Reaction equation

HRID 1604795 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([C:8]2[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[CH:7]=1.Br[C:24]1C=CC([N+]([O-])=O)=CC=1C(OC)=O.COC1C=CC(C)=CC=1B(O)O>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>[CH3:22][O:21][C:5]1[CH:4]=[CH:3][C:2]([CH3:24])=[CH:7][C:6]=1[C:8]1[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 10733357Methyl5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate

Product 1

HCID 23433460Methyl 2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylateYield 98%

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 (1.80 g, 6.92 mmol), (PPh3)4Pd (0.33 g, 0.28 mmol), and 2-methoxy-5-methylphenylboronic acid (1.58 g, 9.51 mmol) to afford 2.03 g (98%) of methyl 2'-methoxy-5'methyl-4-nitro-2-biphenylcarboxylate as a white solid. Data for methyl (2'-methoxy-5'-methyl-4-nitro-2-biphenylcarboxylate): 1H NMR (400 MHz, CDCl3) 8.69 (d, J=2.5, 1H), 8.36 (dd, J=8.4, 2.5, 1H), 7.51 (d, J=8.5, 1H), 7.20 (m, 1H), 7.07 (d, J=2.1, 1H), 6.81 (d, J=8.4, 1H), 3.75 (s, 3H), 3.69 (s, 3H), 2.35 (s, 3H).

Sources & evidence

ORD record
ord-5375344c3438421189c9f615561805f8
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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