Methyl 2-Bromo-5-nitrobenzoate → Methyl 2',5'-dimethoxy-4-nitro-2-biphenylcarboxylate

HRID 1938465Notes

Reaction equation

HRID 1938465 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.BrC1C=CC([N+]([O-])=O)=CC=1[C:26](OC)=[O:27].COC1C=CC(OC)=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>[CH3:20][O:19][C:17]([C:9]1[C:8]([C:6]2[CH:7]=[C:2]([O:27][CH3:26])[CH:3]=[CH:4][C:5]=2[O:21][CH3:22])=[CH:13][CH:12]=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=1)=[O:18]

Participants

5

Reactant 3

HCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 27343422,5-Dimethoxyphenylboronic acidHCID 10733357Methyl5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylate

Product 1

HCID 10805422Methyl 2',5'-dimethoxy-4-nitro-2-biphenylcarboxylateYield 69%

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 (2.46 g, 9.46 mmol), (PPh3)4Pd (0.33 g, 0.28 mmol), and 2,5-dimethoxyphenylboronic acid (2.42 g, 13.3 mmol) to afford 2.08 g (69%) of methyl(2',5'-dimethoxy-4-nitro-2-biphenylcarboxylate) as a white solid. Data for methyl(2',5'-dimethoxy-4-nitro-2-biphenylcarboxylate): 1H NMR (400 MHz, CDCl3) 8.70 (d, J=2.4, 1H), 8.37 (dd, J=8.4, 2.5, 1H), 7.52 (d, J=8.5, 1H), 6.92 (dd, J=8.8, 3.0, 1H), 6.84 (m, 1H), 3.82 (s, 3H), 3.75 (s, 3H), 3.67 (s, 3H).

Sources & evidence

ORD record
ord-b87ddb1d903042699c0ff58e06140a6d
Source dataset
uspto-grants-1997_12
Patent number
US05693647

Reaction notes

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